阅读说明：本技术 有机发光装置 (Organic light emitting device ) 是由 金相范 尹丞希 宋寅范 枝连一志 笹田康幸 于 2021-05-28 设计创作，主要内容包括：本公开涉及有机发光装置。特别地,本公开涉及有机发光二极管和有机发光装置,所述有机发光二极管和有机发光装置中的每一者包括：至少一个发光材料层,所述至少一个发光材料层包含经至少一个氘取代的基于蒽的主体和基于硼的掺杂剂；至少一个电子阻挡层,所述至少一个电子阻挡层包含经芳基取代的基于胺的化合物；以及任选地至少一个空穴阻挡层,所述至少一个空穴阻挡层包含基于嗪的化合物和基于苯并咪唑的化合物中的至少一者。有机发光二极管和有机发光装置具有改善的发光效率和提高的发光寿命。(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 layer of light emitting material 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 oxazine-based compound and a benzimidazole-based compound. The organic light emitting diode and the organic light emitting device have improved light emitting efficiency and increased light emitting life.)

1. An organic light emitting device comprising:

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 a light emitting layer disposed between the first electrode and the second electrode,

wherein the light emitting layer comprises at least one light 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 light emitting material layer,

wherein the at least one light emitting material layer includes a first host of an anthracene-based compound and a first dopant of a boron-based compound,

wherein the anthracene nucleus of the first host is deuterated and the first dopant has a structure of formula 3 below, an

Wherein the at least one electron blocking layer comprises an amine-based compound having the structure of formula 5 below:

[ formula 3]

Wherein R is₁₁To R₁₄Each of (1), R₂₁To R₂₄Each of (1), R₃₁To R₃₅Each of (1) and R₄₁To R₄₅Each of which is independently selected from protium, deuterium, C₁-C₁₀Alkyl radical, C₆-C₃₀Aryl radical, C₆-C₃₀Arylamino and C₅-C₃₀Heteroaryl radical, R₁₁To R₁₄、R₂₁To R₂₄、R₃₁To R₃₅And R₄₁To R₄₅Are the same or different from each other; and R₅₁Selected from protium, deuterium, C₁-C₁₀Alkyl and C₃-C₁₅Cycloalkyl, wherein said C₆-C₃₀Aryl optionally via C₁-C₁₀Alkyl substitution;

[ formula 5]

Wherein R is₆₁To R₆₂And R₆₄Each of which is independently monocyclic aryl or polycyclic aryl, R₆₃Is a monocyclic arylene or polycyclic arylene radical, wherein R₆₁To R₆₄At least one of which is polycyclic.

2. The organic light-emitting device according to claim 1, wherein the anthracene-based compound has the following formula 1:

[ formula 1]

Wherein R is₁And R₂Each of which is independently C₆-C₃₀Aryl or C₅-C₃₀A heteroaryl group; l is₁Is C₆-C₃₀An arylene group; a is 0 or1; and b is an integer from 1 to 8.

3. The organic light-emitting device of claim 1, wherein the first host is selected from the following compounds:

4. the organic light emitting device of claim 1, wherein the first dopant is selected from the following compounds:

5. the organic light-emitting device of claim 1, wherein the amine-based compound is selected from the following compounds:

6. the organic light-emitting device according to claim 1, the light-emitting layer further comprising at least one hole blocking layer disposed between the at least one light-emitting material layer and the second electrode.

7. The organic light-emitting device according to claim 6, wherein the at least one hole blocking layer comprises at least one of an oxazine-based compound having a structure of formula 7 below and a benzimidazole-based compound having a structure of formula 9 below:

[ formula 7]

Wherein Y is₁To Y₅Each of which is independently CR₇₁Or N, Y₁To Y₅One or three of N, and R₇₁Is hydrogen or C₆-C₃₀An aryl group; l is₃Is C₆-C₃₀An arylene group; r₇₂Is C₆-C₃₀Aryl or C₅-C₃₀Heteroaryl, wherein said C₆-C₃₀Aryl optionally via additional C₆-C₃₀Aryl or C₅-C₃₀Heteroaryl substituted, or with C₁₀-C₃₀Condensed aromatic ring or C₁₀-C₃₀The fused heteroaromatic ring forms a spiro structure, wherein the additional C₆-C₃₀Aryl optionally further via other C₆-C₃₀Aryl or C₅-C₃₀Heteroaryl substituted, or with C₁₀-C₃₀Fused aromatic rings form a spiro structure; r₇₃Is hydrogen or R₇₃Form a fused aromatic ring; f is 0 or 1; g is 1 or 2; and h is an integer from 0 to 4;

[ formula 9]

Wherein Ar is C₁₀-C₃₀An arylene group; r₈₁Is C₆-C₃₀Aryl or C₅-C₃₀Heteroaryl of said C₆-C₃₀Aryl and said C₅-C₃₀Each of the heteroaryl groups is optionally via C₁-C₁₀Alkyl substitution; and R₈₂And R₈₃Each of which is independently hydrogen, C₁-C₁₀Alkyl or C₆-C₃₀And (4) an aryl group.

8. The organic light-emitting device of claim 7, wherein the oxazine-based compound is selected from the following compounds:

9. the organic light-emitting device according to claim 7, wherein the benzimidazole-based compound is selected from the group consisting of:

10. the organic light-emitting device according to claim 1, wherein the light-emitting layer further comprises: a first light-emitting portion provided between the first electrode and the second electrode, a second light-emitting portion provided between the first light-emitting portion and the second electrode, and a first charge generation layer provided between the first light-emitting portion and the second light-emitting portion,

wherein the first light emitting part includes a first light emitting material layer, and a first electron blocking layer disposed between the first electrode and the first light emitting material layer,

wherein the second light emitting part includes a second light emitting material layer, an

Wherein at least one of the first and second layers of light emitting material includes the first host and the first dopant.

11. The organic light-emitting device according to claim 10, the second light-emitting portion further comprising a second electron blocking layer disposed between the first charge generation layer and the second light-emitting material layer, and wherein at least one of the first electron blocking layer and the second electron blocking layer comprises an amine-based compound having a structure of formula 5.

12. The organic light emitting device of claim 11, the light emitting layer further comprising at least one of: a first hole blocking layer disposed between the first light emitting material layer and the first charge generation layer, and a second hole blocking layer disposed between the second light emitting material layer and the second electrode.

13. The organic light-emitting device according to claim 12, wherein at least one of the first hole blocking layer and the second hole blocking layer comprises at least one of an oxazine-based compound having a structure of formula 7 below and a benzimidazole-based compound having a structure of formula 9 below:

[ formula 7]

Wherein Y is₁To Y₅Each of which is independently CR₇₁Or N, Y₁To Y₅One or three of N, and R₇₁Is hydrogen or C₆-C₃₀An aryl group; l is₃Is C₆-C₃₀An arylene group; r₇₂Is C₆-C₃₀Aryl or C₅-C₃₀Heteroaryl, wherein said C₆-C₃₀Aryl optionally via additional C₆-C₃₀Aryl or C₅-C₃₀Heteroaryl substituted, or with C₁₀-C₃₀Condensed aromatic ring or C₁₀-C₃₀The fused heteroaromatic ring forms a spiro structure, wherein the additional C₆-C₃₀Aryl optionally further via other C₆-C₃₀Aryl or C₅-C₃₀Heteroaryl substituted, or with C₁₀-C₃₀Fused aromatic rings form a spiro structure; r₇₃Is hydrogen or R₇₃Form a fused aromatic ring; f is 0 or 1; g is 1 or 2; and h is an integer from 0 to 4;

[ formula 9]

Wherein Ar is C₁₀-C₃₀An arylene group; r₈₁Is C₆-C₃₀Aryl or C₅-C₃₀Heteroaryl of said C₆-C₃₀Aryl and theC₅-C₃₀Each of the heteroaryl groups is optionally via C₁-C₁₀Alkyl substitution; and R₈₂And R₈₃Each of which is independently hydrogen, C₁-C₁₀Alkyl or C₆-C₃₀And (4) an aryl group.

14. The organic light-emitting device according to claim 10, wherein the second light-emitting material layer emits yellow-green light or red-green light.

15. The organic light-emitting device according to claim 14, wherein the light-emitting layer further comprises a third light-emitting portion provided between the second light-emitting portion and the second electrode, and a second charge-generation layer provided between the second light-emitting portion and the third light-emitting portion,

wherein the third light emitting part includes a third light emitting material layer, an

Wherein at least one of the first luminescent material layer and the third luminescent material layer includes the first host and the first dopant.

16. The organic light-emitting device according to claim 15, wherein the third light-emitting portion further comprises a third electron-blocking layer disposed between the second charge-generating layer and the third light-emitting material layer, and wherein at least one of the first electron-blocking layer and the third electron-blocking layer comprises an amine-based compound having a structure of formula 5.

17. The organic light emitting device of claim 16, the light emitting layer further comprising at least one of: a first hole blocking layer disposed between the first light emitting material layer and the first charge generation layer, a second hole blocking layer disposed between the second light emitting material layer and the second charge generation layer, and a third hole blocking layer disposed between the third light emitting material layer and the second electrode.

18. The organic light-emitting device according to claim 17, wherein at least one of the first hole blocking layer, the second hole blocking layer, and the third hole blocking layer comprises at least one of an oxazine-based compound having a structure of formula 7 below and a benzimidazole-based compound having a structure of formula 9 below:

[ formula 7]

Wherein Y is₁To Y₅Each of which is independently CR₇₁Or N, Y₁To Y₅One or three of N, and R₇₁Is hydrogen or C₆-C₃₀An aryl group; l is₃Is C₆-C₃₀An arylene group; r₇₂Is C₆-C₃₀Aryl or C₅-C₃₀Heteroaryl, wherein said C₆-C₃₀Aryl optionally via additional C₆-C₃₀Aryl or C₅-C₃₀Heteroaryl substituted, or with C₁₀-C₃₀Condensed aromatic ring or C₁₀-C₃₀The fused heteroaromatic ring forms a spiro structure, wherein the additional C₆-C₃₀Aryl optionally further via other C₆-C₃₀Aryl or C₅-C₃₀Heteroaryl substituted, or with C₁₀-C₃₀Fused aromatic rings form a spiro structure; r₇₃Is hydrogen or R₇₃Form a fused aromatic ring; f is 0 or 1; g is 1 or 2; and h is an integer from 0 to 4;

[ formula 9]

Wherein Ar is C₁₀-C₃₀An arylene group; r₈₁Is C₆-C₃₀Aryl or C₅-C₃₀Heteroaryl of said C₆-C₃₀Aryl and said C₅-C₃₀Each of the heteroaryl groups is optionally via C₁-C₁₀Alkyl substitution; and R₈₂And R₈₃Each of which is independently hydrogen, C₁-C₁₀Alkyl or C₆-C₃₀And (4) an aryl group.

19. The organic light emitting device of claim 1, wherein the substrate defines red, green, and blue pixels, and the organic light emitting diodes are positioned corresponding to the red, green, and blue pixels, and further comprising a color conversion layer disposed between the substrate and the organic light emitting diodes or over the organic light emitting diodes corresponding to the red and green pixels.

20. The organic light emitting device of claim 1, wherein the substrate defines red, green, and blue pixels, and the organic light emitting diodes are positioned corresponding to the red, green, and blue pixels, and further comprising a color filter layer disposed between the substrate and the organic light emitting diodes or over the organic light emitting diodes corresponding to the red, green, and blue pixels.

Technical Field

The present disclosure relates to an organic light emitting device, and more particularly, to an organic light emitting device having excellent light emitting efficiency and light emitting life.

Background

Organic Light Emitting Diodes (OLEDs) among widely used flat panel display devices have been in the spotlight as display devices that rapidly replace liquid crystal display devices (LCDs). The OLED can be formed smaller thanAnd unidirectional or bidirectional images can be realized by the electrode configuration. Furthermore, the OLED may be formed even on a flexible transparent substrate such as a plastic substrate, so that a flexible or foldable display device may be easily implemented using the OLED. In addition, the OLED can be driven at a lower voltage and has excellent high color purity, compared to the LCD.

Since the fluorescent material uses only singlet exciton energy during light emission, the prior art fluorescent material exhibits low light emission efficiency. In contrast, since the phosphorescent material uses triplet exciton energy as well as singlet exciton energy in the light emitting process, it may exhibit high light emitting efficiency. However, metal complexes, which are representative phosphorescent materials, have short emission lifetimes for commercial use. In particular, blue light-emitting materials have not yet exhibited satisfactory light-emitting efficiency and light-emitting lifetime as compared with light-emitting materials of other colors. Therefore, it is required to develop a new compound or device structure that can improve the light emitting efficiency and the light emitting lifetime of the organic light emitting diode.

Disclosure of Invention

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

An aspect of the present disclosure is to provide an organic light emitting device having improved light emitting efficiency and light emitting lifetime.

Additional features and aspects will be set forth in the description which follows, and in part will be obvious from the description, or may be learned by practice of the inventive concepts presented herein. Other features and aspects of the inventive concept may be realized and attained by the structure particularly pointed out in the written description and claims hereof as well as the appended drawings.

To achieve these and other aspects of the inventive concept, as embodied and broadly described, the present disclosure provides an organic light emitting device including: 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 a light emitting layer disposed between the first electrode and the second electrode, wherein the light emitting layer includes at least one light 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 light emitting material layer, wherein the at least one light emitting material layer includes a first host of an anthracene-based compound and a first dopant of a boron-based compound, wherein the anthracene nucleus of the first host is deuterated and the first dopant has a structure of formula 3 below, and wherein the at least one electron blocking layer includes an amine-based compound having a structure of formula 5 below:

[ formula 3]

Wherein R is₁₁To R₁₄Each of (1), R₂₁To R₂₄Each of (1), R₃₁To R₃₅Each of (1) and R₄₁To R₄₅Each of which is independently selected from protium, deuterium, C₁-C₁₀Alkyl radical, C_6-C₃₀Aryl radical, C₆-C₃₀Arylamino and C₅-C₃₀Heteroaryl radical, R₁₁To R₁₄、R₂₁To R₂₄、R₃₁To R₃₅And R₄₁To R₄₅May be the same as or different from each other; and R₅₁Selected from protium, deuterium, C₁-C₁₀Alkyl and C₃-C₁₅Cycloalkyl, wherein said C₆-C₃₀Aryl optionally via C₁-C₁₀Alkyl substitution;

[ formula 5]

Wherein R is₆₁To R₆₂And R₆₄Each of which is independently monocyclic aryl or polycyclic aryl, R₆₃Is a monocyclic arylene or polycyclic arylene radical, wherein R₆₁To R₆₄At least one of which is polycyclic.

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

[ formula 1]

Wherein R is₁And R₂Each of which is independently C₆-C₃₀Aryl or C₅-C₃₀A heteroaryl group; l is₁Is C₆-C₃₀An arylene group; a is 0 or 1; and b is an integer from 1 to 8.

The light emitting layer may further include at least one hole blocking layer or electron transport layer including at least one of an oxazine-based compound and a benzimidazole-based compound.

The light-emitting layer may include a single light-emitting portion or may include a plurality of light-emitting portions to form a serial structure.

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

Such an organic light emitting diode having a series structure may emit blue light, or white light.

The substrate may define red, green, and blue pixels, and the organic light emitting diode may be positioned corresponding to the red, green, and blue pixels, and the organic light emitting device may further include a color conversion layer disposed between the substrate and the organic light emitting diode or above the organic light emitting diode corresponding to the red and green pixels.

The substrate may define red, green, and blue pixels, and the organic light emitting diode may be positioned corresponding to the red, green, and blue pixels, and the organic light emitting device may further include a color filter layer disposed between the substrate and the organic light emitting diode or above the organic light emitting diode corresponding to the red, green, and blue pixels.

It is to be understood that both the foregoing general description and the following detailed description are exemplary and explanatory and are intended to provide further explanation of the inventive concepts claimed.

Drawings

The accompanying drawings, which are included to provide a further understanding of the disclosure and are incorporated in and constitute a part of this application, illustrate embodiments of the disclosure and together with the description serve to explain the principles of the disclosure.

Fig. 1 is a schematic circuit diagram illustrating an organic light emitting display device according to the present disclosure.

Fig. 2 is a sectional view illustrating an organic light emitting display device as an example of an organic light emitting device according to an exemplary aspect of the present disclosure.

Fig. 3 is a sectional view illustrating an organic light emitting diode having a single light emitting part according to an exemplary aspect of the present disclosure.

Fig. 4 is a cross-sectional view illustrating an organic light emitting diode having a dual stack structure according to another exemplary aspect of the present disclosure.

Fig. 5 is a cross-sectional view illustrating an organic light emitting display device according to another exemplary aspect of the present disclosure.

Fig. 6 is a cross-sectional view illustrating an organic light emitting diode having a dual stack structure according to still another exemplary aspect of the present disclosure.

Fig. 7 is a cross-sectional view illustrating an organic light emitting diode having a triple stack structure according to still another exemplary aspect of the present disclosure.

Fig. 8 is a cross-sectional view illustrating an organic light emitting display device according to still another exemplary aspect of the present disclosure.

Detailed Description

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

The organic light emitting diode of the present disclosure may improve its light emitting efficiency and its light emitting life by applying a specific organic compound to at least one light emitting part. The organic light emitting diode may be applied to an organic light emitting device, such as an organic light emitting display device or an organic light emitting lighting device.

Fig. 1 is a schematic circuit diagram illustrating an organic light emitting display device of the present disclosure. As shown in fig. 1, in the organic light emitting display device, a gate line GL, a data line DL, and a power line PL cross each other to define a pixel region P. 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 in 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 to the gate line GL, a data signal applied to the data line DL is applied to the 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 a data signal applied to 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. Then, the organic light emitting diode D emits light having luminance proportional to the current flowing through the driving thin film transistor Td. In this case, the storage capacitor Cst is charged 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. Accordingly, the organic light emitting display device may display a desired image.

Fig. 2 is a schematic cross-sectional view illustrating an organic light emitting display device according to an exemplary aspect of the present disclosure. As shown in fig. 2, the organic light emitting display device 100 includes a substrate 102, a thin film transistor Tr over the substrate 102, and an organic light emitting diode D connected to the thin film transistor Tr. As an example, the substrate 102 defines red, green and blue pixels, and an organic light emitting diode D is positioned in each pixel. In other words, organic light emitting diodes D each emitting red, green, or blue light are correspondingly positioned in the red, green, and blue pixels.

The substrate 102 may include, but is not limited to, glass, thin flexible materials, and/or polymer plastics. For example, the flexible material may be selected from, but not limited to, the group of: polyimide (PI), Polyethersulfone (PES), polyethylene naphthalate (PEN), polyethylene terephthalate (PET), Polycarbonate (PC), and combinations thereof. The substrate 102 over which the thin film transistor Tr and the organic light emitting diode D are disposed forms an array substrate.

A buffer layer 106 may be disposed over the substrate 102, and the thin film transistor Tr is disposed over the buffer layer 106. The buffer layer 106 may be omitted.

A semiconductor layer 110 is disposed over the buffer layer 106. In one exemplary aspect, the semiconductor layer 110 may include, but is not limited to, an oxide semiconductor material. In this case, a light blocking pattern may be disposed under the semiconductor layer 110, and the light blocking pattern may prevent light from being incident toward the semiconductor layer 110, thereby preventing the semiconductor layer 110 from being deteriorated by the light. Alternatively, the semiconductor layer 110 may include polysilicon. In this case, opposite edges of the semiconductor layer 110 may be doped with impurities.

A gate insulating layer 120 including an insulating material is disposed on the semiconductor layer 110. The gate insulating layer 120 may include, but is not limited to, an inorganic insulating material, such as silicon oxide (SiO)_x) Or silicon nitride (SiN)_x)。

A gate electrode 130 made of a conductive material, for example, metal, is disposed over the gate insulating layer 120 corresponding to the center of the semiconductor layer 110. Although the gate insulating layer 120 is disposed over the entire region of the substrate 102 in fig. 2, the gate insulating layer 120 may be patterned the same as the gate electrode 130.

An interlayer insulating layer 140 containing an insulating material is provided on the gate electrode 130, covering over the entire surface of the substrate 102. The interlayer insulating layer 140 may include an inorganic insulating material, for example, silicon oxide (SiO)_x) Or silicon nitride (SiN)_x) (ii) a Or an organic insulating material such as benzocyclobutene or photo-acryl.

The interlayer insulating layer 140 has a first semiconductor layer contact hole 142 and a second semiconductor layer contact hole 144 exposing both sides of the semiconductor layer 110. The first and second semiconductor layer contact holes 142 and 144 are disposed over opposite sides of the gate electrode 130 and spaced apart by the gate electrode 130. The first and second semiconductor layer contact holes 142 and 144 are formed in the gate insulating layer 120 in fig. 2. Alternatively, when the gate insulating layer 120 is patterned identically to the gate electrode 130, the first and second semiconductor layer contact holes 142 and 144 are formed only in the interlayer insulating layer 140.

A source electrode 152 and a drain electrode 154 made of a conductive material such as metal are provided on the interlayer insulating layer 140. The source electrode 152 and the drain electrode 154 are spaced apart from each other with respect to the gate electrode 130, and contact both sides of the semiconductor layer 110 through the first semiconductor layer contact hole 142 and the second semiconductor layer contact hole 144, respectively.

The semiconductor layer 110, the gate electrode 130, the source electrode 152, and the drain electrode 154 constitute a thin film transistor Tr serving as a driving element. The thin film transistor Tr in fig. 2 has a coplanar structure in which the gate electrode 130, the source electrode 152, and the drain electrode 154 are disposed over the semiconductor layer 110. Alternatively, the thin film transistor Tr may have an inverted staggered structure in which a gate electrode is disposed below a semiconductor layer and source and drain electrodes are disposed above the semiconductor layer. In this case, the semiconductor layer may include amorphous silicon.

Although not shown in fig. 2, gate and data lines crossing each other to define a pixel region, and switching elements connected to the gate and data lines may also be formed in the pixel region. The switching element is connected to a thin film transistor Tr as a driving element. Further, the power line is spaced apart in parallel with the gate line or the data line, and the thin film transistor Tr may further include a storage capacitor configured to constantly maintain the voltage of the gate electrode for one frame.

A passivation layer 160 is disposed on the source and drain electrodes 152 and 154 over the entire substrate 102, covering the thin film transistor Tr. The passivation layer 160 has a flat top surface and a drain contact hole 162 exposing the drain electrode 154 of the thin film transistor Tr. Although the drain contact hole 162 is disposed on the second semiconductor layer contact hole 144, it may be spaced apart from the second semiconductor layer contact hole 144.

The Organic Light Emitting Diode (OLED) D includes a first electrode 210 disposed on the passivation layer 160 and connected to the drain electrode 154 of the thin film transistor Tr. The organic light emitting diode D further includes a light emitting layer 230 and a second electrode 220 each sequentially disposed on the first electrode 210.

The first electrode 210 is disposed in each pixel region. The first electrode 210 may be an anode and include a conductive material having a relatively high work function value. For example, the first electrode 210 may 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 device 100 is a top emission type, a reflective electrode or a reflective layer may be disposed under the first electrode 210. For example, the reflective electrode or reflective layer may include, but is not limited to, an aluminum-palladium-copper (APC) alloy.

In addition, a bank layer 164 is disposed on the passivation layer 160 to cover an edge of the first electrode 210. The bank layer 164 exposes the center of the first electrode 210. The bank layer 164 may be omitted.

A light emitting layer 230 is disposed on the first electrode 210. In one exemplary embodiment, the light emitting layer 230 may have a single layer structure of a light emitting material layer. Alternatively, as shown in fig. 3 and 4, the light emitting layer 230 may have a multi-layer structure of a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting material layer, a hole blocking layer, an electron transport layer, and/or an electron injection layer. The light emitting layer 230 may have a single light emitting portion or may have a plurality of light emitting portions to form a serial structure.

The light emitting layer 230 may include at least one light emitting material layer including an anthracene-based host and a boron-based dopant and at least one electron blocking layer including an arylamine-based compound. Alternatively, the light emitting layer 230 may further include at least one hole blocking layer including at least one of an oxazine-based compound and a benzimidazole-based compound. The light emitting layer 230 enables the OLED D and the organic light emitting display device 100 to significantly improve their light emitting efficiency and light emitting life.

A second electrode 220 is disposed over the substrate 102 over which the light emitting layer 230 is disposed. The second electrode 220 may be disposed over the entire display area, and may include a conductive material having a relatively low work function value compared to the first electrode 210, and may be a cathode. For example, the second electrode 220 may include, but is not limited to, aluminum (Al), magnesium (Mg), calcium (Ca), silver (Ag), alloys thereof, or combinations thereof such as aluminum-magnesium alloy (Al-Mg).

In addition, an encapsulation film 170 may be disposed over the second electrode 220 to prevent external moisture from penetrating into the organic light emitting diode D. The encapsulation film 170 may have, but is not limited to, a laminated structure of a first inorganic insulating film 172, an organic insulating film 174, and a second inorganic insulating film 176. The encapsulation film 170 may be omitted.

A polarizing plate may be attached on the encapsulation film to reduce reflection of external light. For example, the polarizing plate may be a circular polarizing plate. In addition, a cover window may be attached to the encapsulation film 170 or the polarizing plate. In this case, the substrate 102 and the cover window have flexible characteristics, so that a flexible display device can be constructed.

As described above, the light emitting layer 230 in the organic light emitting diode D includes a specific compound, so that the organic light emitting diode D can improve its light emitting efficiency and its light emitting life. Fig. 3 is a schematic cross-sectional view illustrating an organic light emitting diode having a single light emitting part according to an exemplary embodiment of the present disclosure.

As shown in fig. 3, an Organic Light Emitting Diode (OLED) D1 according to a first embodiment of the present disclosure includes first and second electrodes 210 and 220 facing each other, and a light emitting layer 230 disposed between the first and second electrodes 210 and 220. In one exemplary embodiment, the light emitting layer 230 includes a light Emitting Material Layer (EML)340 (which may be a first EML) disposed between the first electrode 210 and the second electrode 220, and an Electron Blocking Layer (EBL)330 (which may be a first EBL) as a first exciton blocking layer disposed between the first electrode 210 and the EML 340. Alternatively, the light emitting layer 230 may further include a Hole Blocking Layer (HBL)350 (which may be a first HBL) as a second exciton blocking layer disposed between the EML340 and the second electrode 220.

In addition, the light emitting layer 230 may further include a Hole Injection Layer (HIL)310 disposed between the first electrode 210 and the EBL 330, and a Hole Transport Layer (HTL)320 disposed between the HIL 310 and the EBL 330. In addition, the light emitting layer 230 may further include an Electron Injection Layer (EIL)360 disposed between the HBL 350 and the second electrode 220. In an alternative embodiment, the light emitting layer 230 may further include an Electron Transport Layer (ETL) disposed between the HBL 350 and the EIL 360.

The first electrode 210 may be an anode that provides holes into the EML 340. The first electrode 210 may include a conductive material having a relatively high work function value, such as a Transparent Conductive Oxide (TCO). In one exemplary embodiment, the first electrode 210 may 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 electrode 220 may be a cathode that provides electrons into the EML 340. The second electrode 220 may include a conductive material having a relatively low work function value, i.e., a highly reflective material, such as aluminum (Al), magnesium (Mg), calcium (Ca), silver (Ag), alloys thereof, or combinations thereof, such as an aluminum-magnesium alloy (Al-Mg). For example, each of the first electrode 210 and the second electrode 220 may be laminated at a thickness of about 30nm to about 300nm, but is not limited thereto.

The EML340 includes a host 342 (which may be a first host) of an anthracene-based compound and a dopant 344 (which may be a first dopant) of a boron-based compound, such that the EML340 emits blue light. In this case, the nucleus of body 342 is deuterated. For example, the anthracene nucleus can be partially or fully deuterated. In addition, some or all of the hydrogens in the boron-based compound may be deuterated. That is, the anthracene nucleus of the body 342 is deuterated, and the dopant 344 may not be deuterated or may be partially or fully deuterated. As one example, the host 342 of an anthracene-based compound having a partially or fully deuterated anthracene nucleus may have the structure of formula 1 below:

[ formula 1]

In formula 1, R₁And R₂Each of which is independently C₆-C₃₀Aryl or C₅-C₃₀A heteroaryl group; l is₁Is C₆-C₃₀An arylene group; a is 0 or 1; and b is an integer from 1 to 8.

That is, the anthracene moiety of the host 342 as the core is substituted with deuterium (D), and substituents other than the anthracene moiety are not deuterated. As an example, R₁And R₂Each of which may be independently selected from, but is not limited to, phenyl, naphthyl, fluorenyl, dibenzofuranyl, dibenzothiophenyl, phenanthryl, carbazolyl, and carbolinyl, such as phenyl or naphthyl (e.g., 1-naphthyl or 2-naphthyl). L is₁May be phenylene or naphthylene, and b may be 8.

In one exemplary embodiment, the body 342 may be selected from any one of the structures having the following formula 2:

[ formula 2]

The first dopant 344 of the boron-based compound emitting blue light may have the following structure of formula 3:

[ formula 3]

In formula 3, R₁₁To R₁₄Each of (1), R₂₁To R₂₄Each of (1), R₃₁To R₃₅Each of (1) and R₄₁To R₄₅Each of which is independently selected from protium, deuterium, C₁-C₁₀Alkyl radical, C₆-C₃₀Aryl radical, C₆-C₃₀Arylamino and C₅-C₃₀Heteroaryl radical, R₁₁To R₁₄、R₂₁To R₂₄、R₃₁To R₃₅And R₄₁To R₄₅May be the same as or different from each other; and R₅₁Selected from protium, deuterium, C₁-C₁₀Alkyl and C₃-C₁₅Cycloalkyl, wherein said C₆-C₃₀Aryl optionally via C₁-C₁₀Alkyl substitution.

When can be R₁₁To R₁₄Each of (1), R₂₁To R₂₄Each of (1), R₃₁To R₃₅Each of (1) and R₄₁To R₄₅When the aryl or arylamino group of each of (a) is substituted, the substituent may be, but is not limited to, C₁-C₁₀Alkyl groups such as tert-butyl.

In the boron-based compound as the dopant 344, the benzene ring bonded to the boron atom and the two nitrogen atoms is deuterated (D), C₁-C₁₀Alkyl radical, C₆-C₃₀Aryl and C₆-C₃₀At least one of the arylamino groups is substituted such that the OLED D1 including the dopant 344 has improved light emission characteristics.

For example, it may be R₁₁To R₁₄Each of (1), R₂₁To R₂₄Each of (1), R₃₁To R₃₅Each of (1) and R₄₁To R₄₅The arylamino group of each of may be diphenylamino or phenylnaphthylamino, and may be R₁₁To R₁₄Each of (1), R₂₁To R₂₄Each of (1), R₃₁To R₃₅Each of (1) and R₄₁To R₄₅The aryl group of each of (a) may be phenyl or naphthyl, unsubstituted or substituted with at least one, e.g., 1 to 2, alkyl groups. May be R₁₁To R₁₄Each of (1), R₂₁To R₂₄Each of (1), R₃₁To R₃₅Each of (1) and R₄₁To R₄₅The alkyl group of each of (a) may be C₁-C₅Alkyl radicals such as the methyl, ethyl, propyl, butyl (e.g. tert-butyl) and pentyl radicals, and may be R₁₁To R₁₄Each of (1), R₂₁To R₂₄Each of (1), R₃₁To R₃₅Each of (1) and R₄₁To R₄₅The heteroaryl group of each of may be one of pyridyl, quinolyl, carbazolyl, dibenzofuranyl and dibenzothienylOne of them. In this case, each of the arylamino, aryl, alkyl, and heteroaryl groups can be deuterated.

Furthermore, R₅₁May be selected from protium, deuterium, C₁-C₁₀Alkyl (e.g., methyl, ethyl, propyl, butyl, or pentyl) and adamantyl.

In one exemplary embodiment, R₁₁To R₁₄One of (1), R₂₁To R₂₄One of (1), R₃₁To R₃₅One of (1) and R₄₁To R₄₅Each of which may be independently t-butyl, and R₁₁To R₁₄The remainder of (1), R₂₁To R₂₄The remainder of (1), R₃₁To R₃₅The remainder of (1) and R₄₁To R₄₅Each of the remainder of (a) may be protium or deuterium, and R₅₁May be protium, deuterium or methyl.

In another exemplary embodiment, R₁₁To R₁₄One of (1), R₂₁To R₂₄One of (1), R₃₁To R₃₅One of (1) and R₄₁To R₄₅Each of which may be independently t-butyl, R₃₁To R₃₅The other of which may be tert-butylphenyl, and R₁₁To R₁₄The remainder of (1), R₂₁To R₂₄The remainder of (1), R₃₁To R₃₅The remainder of (1) and R₄₁To R₄₅The remainder of (a) may be protium or deuterium, and R₅₁May be protium, deuterium or methyl.

As an example, the dopant 344 of the boron-based compound may be selected from any of the structures having the following formula 4:

[ formula 4]

In an exemplary embodiment, the boron-based compound dopant 344 may be doped in the EML340 in a proportion of about 1 wt% to about 50 wt%, for example about 1 wt% to about 30 wt%. The EML340 may be laminated at a thickness of about 10nm to about 200nm, preferably about 20nm to about 100nm, and more preferably about 20nm to about 50nm, but is not limited thereto.

The HIL 310 is disposed between the first electrode 210 and the HTL 320, and improves the interface characteristics between the inorganic first electrode 210 and the organic HTL 320. In an exemplary embodiment, the HIL 310 may comprise a hole injection material selected from the group consisting of, but not limited to: 4,4 '-tris (3-methylphenylamino) triphenylamine (MTDATA), 4' -tris (N, N-diphenyl-amino) triphenylamine (NATA), 4 '-tris (N- (naphthalen-1-yl) -N-phenyl-amino) triphenylamine (1T-NATA), 4' -tris (N- (naphthalen-2-yl) -N-phenyl-amino) triphenylamine (2T-NATA), copper phthalocyanine (CuPc), tris (4-carbazolyl-9-yl-phenyl) amine (TCTA), N '-diphenyl-N, N' -bis (1-naphthyl) -1,1 '-biphenyl-4, 4' -diamine (NPB; NPD), 1,4,5,8,9, 11-hexaazatriphenylene hexacarbonitrile (bipyrazine [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-ethylenedioxythiophene) 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 a compound having the structure of formula 12 below:

[ formula 12]

In an alternative embodiment, the HIL 310 may comprise a hole transport material doped with a hole injection material as will be described. In this case, the hole injection material may be doped in the HIL 310 in a proportion of about 1 wt% to about 50 wt%, for example, about 1 wt% to about 30 wt%. The HIL 310 may be omitted according to the OLED D1 characteristics.

The HTL 320 is disposed adjacent to the EBL 330 between the first electrode 210 and the EBL 330. In an exemplary embodiment, the HTL 320 may include a hole transport material selected from the following, but not limited thereto: n, N '-diphenyl-N, N' -bis (3-methylphenyl) -1,1 '-biphenyl-4, 4' -diamine (TPD), npb (npd), N '-bis [4- [ bis (3-methylphenyl) amino ] phenyl ] -N, N' -diphenyl- [1,1 '-biphenyl ] -4, 4' -diamine (DNTPD), 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-bis [4- (N, N' -di (p-Tolyl) Amino) Phenyl) Cyclohexane (TAPC), 3, 5-bis (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-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 a compound having the structure of formula 11 below:

[ formula 11]

In an exemplary embodiment, each of the HIL 310 and the HTL 320 may be laminated at a thickness of about 5nm to about 200nm, for example, about 5nm to about 100nm, but not limited thereto.

The EBL 330 prevents electrons from being transferred from the EML340 to the first electrode 210. EBL 330 may comprise an amine-based compound having the structure of formula 5 below:

[ formula 5]

In formula 5, R₆₁To R₆₂And R₆₄Each of which is independently monocyclic aryl or polycyclic aryl, R₆₃Is a monocyclic arylene or polycyclic arylene radical, wherein R₆₁To R₆₄At least one of which is polycyclic.

As an example, R₆₁To R₆₄At least two of which may be polycyclic. In this case, the monocyclic aryl group may be phenyl, the monocyclic arylene group may be phenylene, and the polycyclic aryl group may be C₁₀-C₂₀Condensed aryl groups, e.g. naphthyl, anthryl, phenanthryl or pyrenyl, and polycyclic arylene groups may be C₁₀-C₂₀Fused arylene groups, such as naphthylene, anthrylene, phenanthrylene or pyrenylene.

For example, EBL 330 may be selected from any arylamine-based compound having the structure of formula 6 below:

[ formula 6]

Alternatively, the OLED D1 may also include an HBL 350, which prevents holes from being transported from the EML340 to the second electrode 220. As an example, HBL 350 may comprise an oxazine-based compound having the structure of formula 7 below and/or a benzimidazole-based compound having the structure of formula 9 below:

[ formula 7]

In formula 7, Y₁To Y₅Each of which is independently CR₇₁Or nitrogen (N), and Y₁To Y₅One or three of N, wherein R₇₁Is hydrogen or C₆-C₃₀And (4) an aryl group. L is₃Is C₆-C₃₀An arylene group; r₇₂Is C₆-C₃₀Aryl or C₅-C₃₀Heteroaryl, wherein said C₆-C₃₀Aryl optionally via additional C₆-C₃₀Aryl or C₅-C₃₀Heteroaryl substituted, or with C₁₀-C₃₀Condensed aromatic ring or C₁₀-C₃₀The fused heteroaromatic ring forms a spiro structure, wherein the additional C₆-C₃₀Aryl optionally further via other C₆-C₃₀Aryl or C₅-C₃₀Heteroaryl substituted, or with C₁₀-C₃₀Fused aromatic rings form a spiro structure; r₇₃Is hydrogen or R₇₃Form a fused aromatic ring; f is 0 or 1; g is 1 or 2; and h is an integer from 0 to 4.

[ formula 9]

In formula 9, Ar is C₁₀-C₃₀An arylene group; r₈₁Is C₆-C₃₀Aryl or C₅-C₃₀Heteroaryl of said C₆-C₃₀Aryl and said C₅-C₃₀Each of the heteroaryl groups is optionally via C₁-C₁₀Alkyl substitution; and R₈₂And R₈₃Each of which is independently hydrogen, C₁-C₁₀Alkyl or C₆-C₃₀And (4) an aryl group.

In an exemplary embodiment, R in formula 7 is constituted₇₂Aryl of (A) may be unsubstituted or substitutedOne step through addition of C₆-C₃₀Aryl or C₅-C₃₀Heteroaryl groups are substituted or form a spiro structure with another fused aromatic or heteroaromatic ring. For example, may be substituted to R₇₂The aryl or heteroaryl group of (A) may be C₁₀-C₃₀Condensed aryl radicals or C₁₀-C₃₀A fused heteroaryl group. R in formula 7₇₃May be fused to form a naphthyl group. In an exemplary embodiment, HBL 350 may be selected from any oxazine-based compound having the structure of formula 8 below:

[ formula 8]

As an example, "Ar" in formula 9 may be naphthylene or anthracenylene, R in formula 9₈₁Can be phenyl or benzimidazolyl, R in formula 9₈₂May be methyl, ethyl or phenyl, and R in formula 9₈₃And may be hydrogen, methyl or phenyl. In an exemplary embodiment, the benzimidazole compound that may be introduced into HBL 350 may be selected from any benzimidazole-based compound having the structure of the following formula 10:

[ formula 10]

In an exemplary embodiment, each of the EBL 335 and HBL 350 may be independently laminated at a thickness of from about 5nm to about 200nm, such as, but not limited to, from about 5nm to about 100 nm.

The compounds having the structures of formulae 7 to 10 have good electron transport properties as well as excellent hole blocking properties. Therefore, HBL 350 including the compound having the structure of formula 7 to formula 10 may be used as a hole blocking layer and an electron transport layer.

In an alternative embodiment, the OLED D1 may also include an Electron Transport Layer (ETL) disposed between the HBL 350 and the EIL 360. In an exemplary embodiment, the ETL may include, but is not limited to, being based onOxadiazole-based compound, triazole-based compound, phenanthroline-based compound, and benzo-based compoundAzole compounds, benzothiazole-based compounds, benzimidazole-based compounds, triazine-based compounds, and the like.

In particular, the ETL may comprise an electron transport material selected from, but not limited to: tris- (8-hydroxyquinolinylaluminum) (Alq)₃) 2-biphenyl-4-yl-5- (4-tert-butylphenyl) -1,3,4-Oxadiazole (PBD), spiro-PBD, lithium quinoline (Liq), 1,3, 5-tris (N-phenylbenzimidazol-2-yl) benzene (TPBi), bis (2-methyl-8-hydroxyquinoline-N1, O8) - (1, 1' -biphenyl-4-yl) aluminum (BALq), 4, 7-diphenyl-1, 10-phenanthroline (Bphen), 2, 9-bis (naphthalen-2-yl) 4, 7-diphenyl-1, 10-phenanthroline (NBphen), 2, 9-dimethyl-4, 7-diphenyl-1, 10-phenanthroline (BCP), 3- (4-biphenyl) -4-phenyl-5-tert-butylphenyl-1, 2, 4-Triazole (TAZ), 4- (naphthalen-1-yl) -3, 5-diphenyl-4H-1, 2, 4-triazole (NTAZ), 1,3, 5-tris (p-pyridin-3-yl-phenyl) benzene (TpPyPB), 2,4, 6-tris (3 '- (pyridin-3-yl) biphenyl-3-yl) 1,3, 5-triazine (TmPPPyTz), poly [9, 9-bis (3' - (N, N-dimethyl) -N-ethylammonium) -propyl) -2, 7-fluorene]-alt-2, 7- (9, 9-dioctylfluorene)](PFNBr), tris (phenylquinoxaline) (TPQ), diphenyl-4-triphenylsilyl-phenylphosphine oxide (TSPO1), 2- [4- (9, 10-di-2-naphthyl-2-anthryl) phenyl]-1-phenyl-1H-benzimidazole (ZADN), 1, 3-bis (9-phenyl-1, 10-phenanthrolin-2-yl) benzene, 1, 4-bis (2-phenyl-1, 10-phenanthrolin-4-yl) benzene (p-bPPhenB) and/or 1, 3-bis (2-phenyl-1, 10-phenanthrolin-4-yl) benzene (m-bPPhenB).

EIL 360 is arranged on HBL350 and the second electrode 220, and the physical characteristics of the second electrode 320 may be improved, and thus the lifetime of the OLED D1 may be improved. In an exemplary embodiment, the EIL 360 can include, but is not limited to, an alkali metal halide or an alkaline earth metal halide, such as LiF, CsF, NaF, BaF₂Etc., and/or organometallic compounds such as lithium benzoate, sodium stearate, etc.

In an alternative embodiment, EIL 360 can be an organic layer doped with an alkali metal (e.g., Li, Na, K, and/or Cs) and/or an alkaline earth metal (e.g., Mg, Sr, Ba, and/or Ra). The organic host for the EIL 360 may be an electron transport material, and the alkali metal or alkaline earth metal may be doped in a ratio of about 1 wt% to about 30 wt%, but is not limited thereto. As one example, each of the ETL and the EIL 360 may be laminated at a thickness of about 10nm to about 200nm, such as about 10nm to 100nm, but not limited thereto.

The OLED D1 can improve its luminous efficiency and can increase its luminous lifetime by: a host 342 of an anthracene-based compound having a structure of formula 1 to formula 2 and a dopant 344 of a boron-based compound having a structure of formula 3 to formula 4 are applied to the EML340, an arylamine-based compound having a structure of formula 5 and formula 6 is applied to the EBL 330, and optionally an oxazine-based compound having a structure of formula 7 to formula 8 and/or a benzimidazole-based compound having a structure of formula 9 to formula 10 is applied to the HBL 350.

In an exemplary first embodiment, the OLED D1 may have a single light emitting part. The OLED according to the present disclosure may have a series structure including a plurality of light emitting parts. Fig. 4 is a schematic cross-sectional view illustrating an organic light emitting diode having two light emitting parts according to another exemplary embodiment of the present disclosure.

As shown in fig. 4, the OLED D2 according to the second embodiment of the present disclosure includes a first electrode 210 and a second electrode 220 facing each other and a light emitting layer 230A disposed between the first electrode 210 and the second electrode 220. The light emitting layer 230A includes a first light emitting part 400 disposed between the first electrode 210 and the second electrode 220, a second light emitting part 500 disposed between the first light emitting part 400 and the second electrode 220, and a Charge Generation Layer (CGL)470 disposed between the first light emitting part 400 and the second light emitting part 500.

The first electrode 210 may be an anode and include a conductive material having a relatively large work function value, for example, a Transparent Conductive Oxide (TCO) such as ITO, IZO, SnO, ZnO, ICO, AZO, or the like. The second electrode 220 may be a cathode and include a conductive material having a relatively small work function value, such as Al, Mg, Ca, Ag, an alloy thereof, or a combination thereof.

The first light emitting part 400 includes a first light emitting material layer (EML1)440 disposed between the first electrode 210 and the CGL470, and may further include a first electron blocking layer (EBL1)430 disposed between the first electrode 210 and the EML 1440, and optionally a first hole blocking layer (HBL1)450 disposed between the EML 1440 and the CGL 470. In addition, the first light emitting part 400 may further include a Hole Injection Layer (HIL)410 disposed between the first electrode 210 and the EBL 1430, and a first hole transport layer (HTL1)420 disposed between the HIL 410 and the EBL 1430.

The second light emitting part 500 includes a second light emitting material layer (EML2)540 disposed between the CGL470 and the second electrode 220, and may further include a second electron blocking layer (EBL2)530 disposed between the CGL470 and the EML 2540, and optionally a second hole blocking layer (HBL2)550 disposed between the EML 2540 and the second electrode 220. In addition, the second light emitting part 500 may further include a second hole transport layer (HTL2)520 disposed between the CGL470 and the EBL 2530 and an Electron Injection Layer (EIL)560 disposed between the HBL 2550 and the second electrode 220.

As one example, each of the EML 1440 and EML 2540 may independently include a host 442 or 542 (which may be a first host) of an anthracene-based compound having a structure of formula 1 to formula 2, and a dopant 444 or 544 (which may be a first dopant) of a boron-based compound having a structure of formula 3 to formula 4. Although the anthracene nucleus of either host 442 or host 542 of the anthracene-based compound is partially or fully deuterated, dopant 444 or dopant 544 of the boron-based compound may not be deuterated or some or all of the hydrogen may be deuterated. In this case, the OLED D2 emits blue light. The host 442 in the EML 1440 may be the same or different than the host 542 in the EML 2540, and the dopant 444 in the EML 1440 may be the same or different than the dopant 544 in the EML 2540.

The HIL 410 is disposed between the first electrode 210 and the HTL 1420 and improves the interface characteristics between the inorganic first electrode 210 and the organic HTL 1420. In an exemplary embodiment, HIL 410 comprises a hole injection material selected from the group consisting of, but not limited to: 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 compounds having the structure of formula 12. In an alternative embodiment, the HIL 410 may comprise a hole transport material doped with a hole injection material. The HIL 410 may be omitted according to the OLED D2 characteristics.

Each of the HTLs 1420 and 2520 may independently include a hole transport material selected from the following, but not limited thereto: 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 a compound having the structure of formula 11. Each of the HIL 410, HTL 1420, and HTL 2520 may be laminated at a thickness of about 5nm to about 200nm, for example, about 5nm to about 100nm, but is not limited thereto.

Each of the EBLs 1430 and 2530 prevents electrons from being transmitted from the EML 1440 or EML 2540 to the first electrode 210 or CGL470, respectively. As one example, each of the EBL 1430 and the EBL 2530 may independently include an arylamine-based compound having the structure of formula 5 to formula 6.

Each of the HBLs 1450 and 2550 prevents holes from being transmitted from the EML 1440 or EML 2540 to the CGL470 or the second electrode 220, respectively. As one example, each of HBL 1450 and HBL 2550 may independently comprise an oxazine-based compound having a structure of formula 7 to formula 8 and/or a benzimidazole-based compound having a structure of formula 9 to formula 10. Each of the EBL 1430, EBL 2530, HBL 1450 and HBL 2550 may be laminated at a thickness of about 5nm to about 200nm, such as, but not limited to, about 5nm to about 100 nm.

As described above, the compounds having the structures of formulae 7 to 10 have excellent electron transport characteristics and excellent hole blocking characteristics. Thus, each of HBL 1450 and HBL 2550 can function as a hole blocking layer and an electron transport layer.

In an alternative embodiment, the first light emitting part 400 may further include a first electron transport layer (ETL1) disposed between the HBL 1450 and the CGL470 and/or the second light emitting part 500 may further include a second electron transport layer (ETL2) disposed between the HBL 2550 and the EIL 560. Each of ETL1 and ETL2 may independently include, but are not limited to being based onOxadiazole-based compound, triazole-based compound, phenanthroline-based compound, and benzo-based compoundAzole compounds, benzothiazole-based compounds, benzimidazole-based compounds, triazine-based compounds, and the like.

In an exemplary embodiment, each of ETL1 and ETL2 may independently comprise an electron transport material selected from, but not limited to: alq₃PDB, spiro-PBD, Liq, TPBi, BALq, Bphen, NBphen, BCP, TAZ, NTAZ, TpPyPB, TmPPPyTz, PFNBr, TPQ, TSPO1, ZADN, p-bphenB and/or m-bphenB.

The EIL 560 is disposed between the HBL 2550 and the second electrode 220. In an exemplary embodiment, the EIL 560 can include, but is not limited to, an alkali metal halide or an alkaline earth metal halide, such as LiF, CsF, NaF, BaF₂Etc., and/or organometallic compounds such as lithium benzoate, sodium stearate, etc. In an alternative embodiment, the EIL 560 can include an organic layer doped with an alkali metal (e.g., Li, Na, K, and/or Cs) and/or an alkaline earth metal (e.g., Mg, Sr, Ba, and/or Ra). The organic host for the EIL 560 may be an electron transport material, and the alkali metal or alkaline earth metal may be doped in a ratio of about 1 wt% to about 30 wt%, but is not limited thereto. As one example, each of ETL1, ETL2, and EIL 560 may be laminated at a thickness of about 10nm to about 200nm, such as, but not limited to, about 10nm to 100 nm.

The CGL470 is disposed between the first and second light emitting parts 400 and 500. The CGL470 includes an N-type CGL480 disposed adjacent to the first light emitting part 400 and a P-type CGL 490 disposed adjacent to the second light emitting part 500. The N-type CGL480 injects electrons into the first light emitting part 400, and the P-type CGL 490 injects holes into the second light emitting part 500.

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

The P-type CGL 490 may include, but is not limited to, a member selected from tungsten oxide (WO)_x) Molybdenum oxide (MoO)_x) Beryllium oxide (Be)₂O₃) Vanadium oxide (V)₂O₅) And combinations thereof, and/or an organic material selected from the group consisting of NPD, HAT-CN, F4TCNQ, TPD, N '-tetranaphthyl-benzidine (TNB), TCTA, N' -dioctyl-3, 4,9, 10-perylenedicarboximide (PTCDI-C8), and combinations thereof.

The OLED D2 according to the second embodiment of the present disclosure may improve its light emitting efficiency and may improve its light emitting life by: applying an anthracene-based compound having a structure of formula 1 to formula 2 as a first host and a boron-based compound having a structure of formula 3 to formula 4 as a first dopant to the EML 1440 and EML 2540, applying an arylamine-based compound having a structure of formula 5 and formula 6 to the EBL 1430 and the EBL 2530, and optionally applying an oxazine-based compound having a structure of formula 7 to formula 8 and/or a benzimidazole-based compound having a structure of formula 9 to formula 10 to the HBL 1450 and HBL 2550. Further, the organic light emitting display device 100 (see fig. 2) can realize an image having high color purity by combining two light emitting parts each emitting blue light, i.e., a double stacked structure of the light emitting part 400 and the light emitting part 500.

In the second embodiment, the OLED D2 has a series structure of two light emitting parts. Alternatively, the OLED may include three light emitting parts, and in addition to the EIL 560, the OLED further includes a second CGL and a third light emitting part disposed on the second light emitting part 500 (see fig. 7).

In the above embodiments, the organic light emitting display device 100 and the OLED D1 and the OLED D2 realized blue (B) light emission. Alternatively, the organic light emitting display device and the OLED may implement a full color display device including white (W) light emission. Fig. 5 is a schematic cross-sectional view illustrating an organic light emitting display device according to another exemplary embodiment of the present disclosure.

As shown in fig. 5, the organic light emitting display device 600 includes: a first substrate 602 defining each of red, green and blue pixels RP, GP and BP; a second substrate 604 facing the first substrate 602; a thin film transistor Tr over the first substrate 602; an organic light emitting diode D disposed between the first and second substrates 602 and 604 and emitting white (W) light; and a color filter layer 680 disposed between the organic light emitting diode D and the second substrate 604.

Each of the first substrate 602 and the second substrate 604 may include, but is not limited to, glass, flexible materials, and/or polymer plastics. For example, each of the first and second substrates 602 and 604 may be made of PI, PES, PEN, PET, PC, and combinations thereof. The first substrate 602 over which the thin film transistor Tr and the organic light emitting diode D are disposed forms an array substrate.

A buffer layer 606 may be disposed over the first substrate 602, and a thin film transistor Tr is disposed over the buffer layer 606 corresponding to each of the red, green, and blue pixels RP, GP, and BP. The buffer layer 606 may be omitted.

A semiconductor layer 610 is disposed over the buffer layer 606. The semiconductor layer 610 may be made of an oxide semiconductor material or polysilicon.

An insulating material (e.g., an inorganic insulating material such as silicon oxide (SiO)) is provided on the semiconductor layer 610_x) Or silicon nitride (SiN)_x) ) of the gate insulating layer 620.

A gate electrode 630 made of a conductive material (e.g., metal) is disposed over the gate insulating layer 620 to correspond to the center of the semiconductor layer 610. An insulating material (e.g., an inorganic insulating material such as silicon oxide (SiO)) is provided on the gate electrode 630_x) Or silicon nitride (SiN)_x) Or an organic insulating material such as benzocyclobutene or photo-acryl).

The interlayer insulating layer 640 has a first semiconductor layer contact hole 642 and a second semiconductor layer contact hole 644 exposing both sides of the semiconductor layer 610. The first and second semiconductor layer contact holes 642 and 644 are disposed over opposite sides of the gate electrode 630 and spaced apart from the gate electrode 630.

A source electrode 652 and a drain electrode 654 made of a conductive material such as metal are provided on the interlayer insulating layer 640. The source electrode 652 and the drain electrode 654 are spaced apart from each other with respect to the gate electrode 630 and contact both sides of the semiconductor layer 610 through the first semiconductor layer contact hole 642 and the second semiconductor layer contact hole 644, respectively.

The semiconductor layer 610, the gate electrode 630, the source electrode 652, and the drain electrode 654 constitute a thin film transistor Tr serving as a driving element.

Although not shown in fig. 5, gate and data lines crossing each other to define a pixel region, and a switching element connected to the gate and data lines may also be formed in the pixel region. The switching element is connected to a thin film transistor Tr as a driving element. Further, the power line is spaced apart in parallel with the gate line or the data line, and the thin film transistor Tr may further include a storage capacitor configured to constantly maintain the voltage of the gate electrode for one frame.

A passivation layer 660 is disposed on the source and drain electrodes 652 and 654 over the entire first substrate 602, covering the thin film transistor Tr. The passivation layer 660 has a drain contact hole 662 exposing the drain electrode 654 of the thin film transistor Tr.

An Organic Light Emitting Diode (OLED) D is positioned over the passivation layer 660. The OLED D includes a first electrode 710 connected to the drain electrode 654 of the thin film transistor Tr, a second electrode 720 facing the first electrode 710, and a light emitting layer 730 disposed between the first electrode 710 and the second electrode 720.

The first electrode 710 formed for each pixel region may be an anode and may include a conductive material having a relatively high work function value. For example, the first electrode 710 may 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 electrode 710. For example, the reflective electrode or reflective layer may include, but is not limited to, an APC alloy.

A bank layer 664 is disposed on the passivation layer 660 to cover an edge of the first electrode 710. The bank layer 664 exposes the center of the first electrode 710 corresponding to each of the red, green, and blue pixels RP, GP, and BP. The bank layer 664 may be omitted.

A light-emitting layer 730 including a light-emitting portion is provided over the first electrode 710. As shown in fig. 6 and 7, the light-emitting layer 730 may include a plurality of light-emitting portions, that is, a light-emitting portion 800, a light-emitting portion 900, a light-emitting portion 1000, a light-emitting portion 1100, and a light-emitting portion 1200, and a plurality of charge generation layers, that is, a charge generation layer 870, a charge generation layer 1070, and a charge generation layer 1170. Each of the light emitting part 800, the light emitting part 900, the light emitting part 1000, the light emitting part 1100, and the light emitting part 1200 includes a light 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.

A second electrode 720 is disposed over the first substrate 602 over which the light emitting layer 730 is disposed. The second electrode 720 may be disposed over the entire display area, and may include a conductive material having a relatively low work function value compared to the first electrode 710, and may be a cathode. For example, the second electrode 720 may include, but is not limited to, aluminum (Al), magnesium (Mg), calcium (Ca), silver (Ag), alloys thereof, or combinations thereof such as aluminum-magnesium alloy (Al-Mg).

Since light emitted from the light emitting layer 730 is incident to the color filter layer 680 through the second electrode 720 in the organic light emitting display device 600 according to the second embodiment of the present disclosure, the second electrode 720 has a thin thickness so that light can be transmitted.

The color filter layer 680 is disposed over the OLED D and includes a red color filter 682, a green color filter 684, and a blue color filter 686 each disposed corresponding to the red pixel RP, the green pixel GP, and the blue pixel BP, respectively. Although not shown in fig. 5, the color filter layer 680 may be attached to the OLED D by an adhesive layer. Alternatively, the color filter layer 680 may be directly disposed on the OLED D.

In addition, an encapsulation film may be disposed over the second electrode 720 to prevent external 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 170 in fig. 2). In addition, a polarizing plate may be attached on the second substrate 604 to reduce reflection of external light. For example, the polarizing plate may be a circular polarizing plate.

In fig. 5, light emitted from the OLED D is transmitted through the second electrode 720, and the color filter layer 680 is disposed over the OLED D. Alternatively, light emitted from the OLED D is transmitted through the first electrode 710, and the color filter layer 680 may be disposed between the OLED D and the first substrate 602. In addition, a color conversion layer may be formed between the OLED D and the color filter layer 680. The color conversion layer may include a red conversion layer, a green conversion layer, and a blue conversion layer each disposed corresponding to the respective pixels (RP, GP, and BP), respectively, to convert white (W) color light into each of red, green, and blue color light, respectively.

As described above, the white (W) color light emitted from the OLED D is transmitted through the red, green, and blue color filters 682, 684, and 686 each disposed corresponding to the red, green, and blue pixels RP, GP, and BP, respectively, so that red, green, and blue light is displayed in the red, green, and blue pixels RP, GP, and BP.

Fig. 6 is a schematic cross-sectional view illustrating an organic light emitting diode having a series structure of two light emitting parts. As shown in fig. 6, an Organic Light Emitting Diode (OLED) D3 according to an exemplary embodiment includes first and second electrodes 710 and 720, and an emission layer 730 disposed between the first and second electrodes 710 and 720. The light emitting layer 730 includes a first light emitting part 800 disposed between the first electrode 710 and the second electrode 720, a second light emitting part 900 disposed between the first light emitting part 800 and the second electrode 720, and a Charge Generation Layer (CGL)870 disposed between the first light emitting part 800 and the second light emitting part 900.

The first light emitting part 800 includes a first light emitting material layer (EML1)840 disposed between the first electrode 710 and the CGL870, and may further include a first electron blocking layer (EBL1)830 disposed between the first electrode 710 and the EML 1840, and optionally a first hole blocking layer (HBL1)850 disposed between the EML 1840 and the CGL 870. In addition, the first light emitting part 800 may further include a Hole Injection Layer (HIL)810 disposed between the first electrode and the EBL 1830 and a first hole transport layer (HTL1)820 disposed between the HIL 810 and the EBL 1830.

The EML 1840 includes a first body 842 of an anthracene-based compound and a first dopant 844 of a boron-based compound. Although the anthracene nucleus in the first body 842 of the anthracene-based compound is partially or fully deuterated, the first dopant 844 of the boron-based compound may not be deuterated or some or all of the hydrogen may be deuterated. The EML 1840 emits blue light.

The EBL 1830 may include an arylamine-based compound having a structure of formula 5 to formula 6. The HBL 1850 may comprise an oxazine-based compound having a structure of formula 7 to formula 8 and/or a benzimidazole-based compound having a structure of formula 9 to formula 10. As described above, the compounds having the structures of formulae 7 to 10 have excellent electron transport characteristics and excellent hole blocking characteristics. Therefore, the HBL 1850 can be used as a hole blocking layer and an electron transport layer.

In an alternative embodiment, the first light emitting part 800 may further include a first electron transport layer (ETL1) disposed between the HBL 1850 and the CGL 870.

The second light emitting part 900 includes a second light emitting material layer (EML2)940 disposed between the CGL870 and the second electrode 720, and may further include a second hole transport layer (HTL2)920 disposed between the CGL870 and the EML 2940 and a second electron transport layer (ETL2) disposed between the EML 2940 and the second electrode 720. In addition, the second light emitting section 900 may further include a second electron blocking layer (EBL2)930 disposed between the HTL 2920 and the EML 2940, a second hole blocking layer (HBL2)950 disposed between the EML 2940 and the ETL2, and an Electron Injection Layer (EIL)960 disposed between the ETL2 and the second electrode 720.

In one exemplary embodiment, EML 2940 may emit red-green (RG) light. In this case, the EML 2940 may include a second body 942, a second dopant 944 that is a green dopant, and a third dopant 946 that is a red dopant. For example, each of the second dopant 944 and the third dopant 946 can be a fluorescent material, a phosphorescent material, and/or a delayed fluorescence material, respectively.

As an example, the second host 942 in the EML 2940 may include, but is not limited to, 9 ' -diphenyl-9H, 9 ' H-3,3 ' -bicarbazole (BCzPh), CBP, 1,3, 5-tris (carbazol-9-yl) benzene (TCP), TCTA, 4 ' -bis (carbazol-9-yl) -2,2 ' -dimethylbiphenyl (CDBP), 2, 7-bis (carbazol-9-yl) -9, 9-dimethylfluorene (DMFL-CBP), 2 ', 7,7 ' -tetrakis (carbazol-9-yl) -9, 9-spirofluorene (spiro-CBP), bis [2- (diphenylphosphino) phenyl ] 9, 9-spirofluorene (spiro-CBP), and the like]Ether oxide (DPEPO), 4 '- (9H-carbazol-9-yl) biphenyl-3, 5-dinitrile (PCzB-2CN), 3' - (9H-carbazol-9-yl) biphenyl-3, 5-dinitrile (mCzB-2CN), 3, 6-bis (carbazol-9-yl) -9- (2-ethyl-hexyl) -9H-carbazole (TCz1), bis (2-hydroxyphenyl) pyridine) beryllium (Bepp)₂) Bis (10-hydroxybenzo [ h ]]Quinoline) beryllium (Bebq)₂) And/or 1,3, 5-tris (1-pyrenyl) benzene (TPB3), and the like.

The second dopant 944, which is a green dopant, may include, but is not limited to [ bis (2-phenylpyridine ]](pyridyl-2-benzofuro [2,3-b ]]Pyridine) iridium, facial-tris (2-phenylpyridine) iridium (III) (facial-Ir (ppy)₃) Bis (2-phenylpyridine) (acetylacetone) iridium (III) (Ir (ppy)₂(acac)), tris [2- (p-tolyl) pyridine]Iridium (III) (Ir (mppy)₃) Bis (2- (naphthalen-2-yl) pyridine) (acetylacetone) iridium (III) (Ir (npy))₂acac), tris (2-phenyl-3-methyl-pyridine) iridium (Ir (3mppy)₃) And/or iridium (III) tris (2- (3-p-xylyl) phenyl) pyridine (TEG).

Third dopant as red dopant946 can include, but are not limited to [ bis (2- (4, 6-dimethyl) phenylquinoline)]Iridium (III) (2,2,6, 6-tetramethylhepta-3, 5-diketonate), bis [2- (4-n-hexylphenyl) quinoline](Acetylacetone) Iridium (III) (Hex-Ir (phq)₂(acac)), tris [2- (4-n-hexylphenyl) quinoline]Iridium (III) (Hex-Ir (phq)₃) Tris [ 2-phenyl-4-methylquinoline ]]Iridium (III) (Ir (Mphq)₃) Bis (2-phenylquinoline) (2,2,6, 6-tetramethylhepta-3, 5-diketonic acid) iridium (III) (Ir (dpm) PQ₂) Bis (phenylisoquinoline) (2,2,6, 6-tetramethylheptan-3, 5-dionate) iridium (III) (Ir (dpm) (piq)₂) Bis [ (4-n-hexylphenyl) isoquinoline](Acetylacetone) Iridium (III) (Hex-Ir (piq)₂(acac)), tris [2- (4-n-hexylphenyl) quinoline]Iridium (III) (Hex-Ir (piq)₃) Tris (2- (3-methylphenyl) -7-methyl-quinoline) iridium (Ir (dmpq)₃) Bis [2- (2-methylphenyl) -7-methyl-quinoline](Acetylacetone) Iridium (III) (Ir (dmpq)₂(acac)) and/or bis [2- (3, 5-dimethylphenyl) -4-methyl-quinoline](Acetylacetone) Iridium (III) (Ir (mphmq)₂(acac))。

In an alternative embodiment, EML 2940 may emit yellow-green (YG) light. In this case, the EML 2940 may include a second host, a second dopant as a green dopant, and a third dopant as a yellow dopant.

The second host for emitting yellow-green color and the second dopant as the green dopant may be the same as the host for emitting red-green (RG) light and the green dopant, 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-diphenylnaphthacene (TBRb), bis (2-phenylbenzothiazole) (acetylacetone) iridium (iii) (ir (bt))₂(acac)), bis (2- (9, 9-diethoxy-fluoren-2-yl) -1-phenyl-1H-benzo [ d-]Imidazole) (acetylacetone) Iridium (III) (Ir (fbi)₂(acac)), bis (2-phenylpyridine) (3- (pyridin-2-yl) -2H-chromen-2-one) iridium (III) (face-Ir (ppy)₂Pc) and/or bis (2- (2, 4-difluorophenyl) quinoline) (picolinic acid) iridium (iii) (FPQIrpic).

When the EML 2940 emits red-green (RG) light or yellow-green (YG) light, each of the second and third dopants may be doped in the EML 2940 in a proportion of about 1 wt% to about 50 wt%, for example about 1 wt% to about 30 wt%.

EBL 2930 may include, but is not limited to, TCTA, tris [4- (diethylamino) phenyl ] amine, N- (biphenyl-4-yl) -9, 9-dimethyl-N- (4- (9-phenyl-9H-carbazol-3-yl) phenyl) -9H-fluoren-2-amine, TAPC, MTDATA, 1, 3-bis (carbazol-9-yl) benzene (mCP), 3, 3-bis (9H-carbazol-9-yl) biphenyl (mCBP), CuPc, DNTPD, TDAPB, DCDPA, 2, 8-bis (9-phenyl-9H-carbazol-3-yl) dibenzo [ b, d ] thiophene and/or 3, 6-bis (N-carbazolyl) -N-phenyl-carbazole.

HBL 2950 may include but is not limited to based onOxadiazole-based compound, triazole-based compound, phenanthroline-based compound, and benzo-based compoundAzole compounds, benzothiazole-based compounds, benzimidazole-based compounds, triazine-based compounds, and the like. For example, the HBL 2950 may comprise a compound having a relatively low HOMO energy level compared to the EML 2940. HBL 2950 may include, but is not limited to BCP, BALq, Alq₃PBD, spiro-PBD, Liq, bis-4, 5- (3, 5-di-3-pyridylphenyl) -2-methylpyrimidine (B3PYMPM), DPEPO, TSPO1, 9- (6- (9H-carbazol-9-yl) pyridin-3-yl) -9H-3, 9' -bicarbazole, and combinations thereof.

The CGL870 is disposed between the first and second light emitting parts 800 and 900. CGL870 may be a PN junction charge generating layer including N-CGL880 and P-CGL 890. That is, the CGL870 includes an N-CGL880 disposed adjacent to the first light emitting part 800 and a P-CGL890 disposed adjacent to the second light emitting part 900.

The OLED D3 according to the third embodiment of the present disclosure may improve its light emitting efficiency and may improve its light emitting life by: the first body 842 of the anthracene-based compound having the structure of formula 1 to formula 2 and the first dopant 844 of the boron-based compound having the structure of formula 3 to formula 4 are applied to the EML 1840, the arylamine-based compound having the structure of formula 5 and formula 6 is applied to the EBL 1830, optionally the oxazine-based compound having the structure of formula 7 to formula 8 and/or the benzimidazole-based compound having the structure of formula 9 to formula 10 is applied to the HBL 1850, and the red-green or yellow-green fluorescent material is applied to the EML 2940. In particular, the OLED D3 includes a dual stack structure in which a first light emitting part 800 emitting blue (B) light and a second light emitting part 900 emitting red-green (RG) light or yellow-green (YG) light are laminated, so that the organic light emitting display device 600 (see fig. 5) can emit white light (W).

In an alternative embodiment, the EML 1840 disposed between the first electrode 710 and the CGL870 may be a red green light emitting material layer or a yellow green light emitting material layer, and the EML 2940 disposed between the CGL870 and the second electrode 720 may be a blue light emitting material layer including a first host of an anthracene-based compound and a first dopant of a boron-based compound.

Alternatively, the organic light emitting diode may have a triple stack structure. Fig. 7 is a schematic cross-sectional view illustrating an organic light emitting diode according to still another exemplary aspect of the present disclosure. As shown in fig. 7, the Organic Light Emitting Diode (OLED) D4 includes a first electrode 710 and a second electrode 720 facing each other, and an emission layer 730A disposed between the first electrode 710 and the second electrode 720. The light-emitting layer 730A includes a first light-emitting portion 1000 disposed between the first electrode 710 and the second electrode 720, a second light-emitting portion 1100 disposed between the first light-emitting portion 1000 and the second electrode 720, a third light-emitting portion 1200 disposed between the second light-emitting portion 1100 and the second electrode 720, a first charge generation layer (CGL1)1070 disposed between the first light-emitting portion 1000 and the second light-emitting portion 1100, and a second charge generation layer (CGL2)1170 disposed between the second light-emitting portion 1100 and the third light-emitting portion 1200.

At least one of the first, second, and third light emitting parts 1000, 1100, and 1200 may emit blue (B) light, and at least another one of the first, second, and third light emitting parts 1000, 1100, and 1200 may emit red-green (RG) light or yellow-green (YG) light. Hereinafter, the OLED D4 in which the first and third light emitting parts 1000 and 1200 emit blue (B) light and the second light emitting part 1100 emits red-green (RG) light or yellow-green (YG) light will be described.

The first electrode 710 may be an anode injecting holes and may include a conductive material having a relatively large work function value, for example, a Transparent Conductive Oxide (TCO) such as ITO, IZO, SnO, ZnO, ICO, AZO, or the like. The second electrode 720 may be a cathode injecting electrons and may include a conductive material having a relatively small work function value, such as Al, Mg, Ca, Ag, an alloy thereof, or a combination thereof.

The first light emitting part 1000 includes a first light emitting material layer (EML1)1040 disposed between the first electrode 710 and the CGL 11070, and may further include a first electron blocking layer (EBL1)1030 disposed between the first electrode 710 and the EML 11040, and optionally a first hole blocking layer (HBL1)1050 disposed between the EML 11040 and the CGL 11070. In addition, the first light emitting part 1000 may further include a Hole Injection Layer (HIL)1010 disposed between the first electrode 710 and the EBL 11030, a first hole transport layer (HTL1)1020 disposed between the HIL 1010 and the EBL 11030, and a first electron transport layer (ETL1) optionally disposed between the HBL 11050 and the CGL 11070.

The second light emitting region 1100 includes a second light emitting material layer (EML2)1140 disposed between the CGL 11070 and the CGL 21170, and may further include a second hole transport layer (HTL2)1120 disposed between the CGL 1070 and the EML 21140, and a second electron transport layer (ETL2) disposed between the EML 21140 and the CGL 21170. In addition, the second light emitting section 1100 may further include a second electron blocking layer (EBL2)1130 disposed between the HTL 21120 and the EML 21140 and/or a second hole blocking layer (HBL2)1150 disposed between the EML 21140 and the ETL 2.

The third light emitting region 1200 includes a third light emitting material layer (EML3)1240 disposed between the CGL 21170 and the second electrode 720, and may further include a third electron blocking layer (EBL3)1230 disposed between the CGL 21170 and the EML 31240, and optionally a third hole blocking layer (HBL3)1250 disposed between the EML 31240 and the second electrode 720. In addition, the third light emitting part 1200 may further include a third hole transport layer (HTL3)1220 disposed between the CGL 21170 and the EBL 31230, an Electron Injection Layer (EIL)1260 disposed between the HBL 31250 and the second electrode 720, and optionally, a third electron transport layer (ETL3) disposed between the HBL 31250 and the EIL 1260.

Each of EML 11040 and EML 31240 may include: a first body 1042 or a first body 1242 which is an anthracene-based compound having a structure of formula 1 to formula 2, and a first dopant 1044 or a first dopant 1244 which is a boron-based compound having a structure of formula 3 to formula 4. Although the anthracene nucleus of each of the first body 1042 and the first body 1242 of the anthracene-based compound is partially or fully deuterated, each of the first dopant 1044 and the first dopant 1244 of the boron-based compound may not be deuterated or some or all of the hydrogen of the boron-based compound may be deuterated. The first body 1042 in the EML 11040 may be the same as or different from the first body 1242 in the EML 31240, and the first dopant 1044 in the EML 11040 may be the same as or different from the first dopant 1244 in the EML 31240. Each of the EML 11040 and the EML 31240 emits blue (B) light.

Each of the EBL 11030 and EBL 31230 may include an arylamine-based compound having a structure of formulae 5 to 6, respectively. Each of the HBL 11050 and HBL 31250 may include an oxazine-based compound having a structure of formula 7 through formula 8 and/or a benzimidazole-based compound having a structure of formula 9 through formula 10, respectively. As described above, the compounds having the structures of formulae 7 to 10 have excellent electron transport characteristics and excellent hole blocking characteristics. Therefore, each of HBL 11050 and HBL 31250 can function as a hole blocking layer and an electron transport layer.

In one exemplary embodiment, the EML 21140 may emit red-green (RG) light. In this case, the EML 21140 may include a second body 1142, a second dopant 1144 of a green dopant, and a third dopant 1146 of a red dopant.

In an alternative embodiment, EML 21140 may emit yellow-green (YG) light. In this case, the EML 21140 may include a second body 1142, a second dopant 1144 as a green dopant, and a third dopant 1146 as a yellow dopant. The second body 1142, the second dopant 1144, and the third dopant 1146 in the EML 21140 emitting Red Green (RG) color or Yellow Green (YG) color may be the same as the materials described above.

When the EML 21140 emits red-green (RG) light or yellow-green (YG) light, the second dopant 1144 and the third dopant 1146 may be doped in the EML 21140 in a proportion of about 1 wt% to about 50 wt%, for example, about 1 wt% to about 30 wt%.

EBL 21130 may include, but is not limited to, TCTA, tris [4- (diethylamino) phenyl ] amine, N- (biphenyl-4-yl) -9, 9-dimethyl-N- (4- (9-phenyl-9H-carbazol-3-yl) phenyl) -9H-fluoren-2-amine, TAPC, MTDATA, mCP, mCBP, CuPc, DNTPD, TDAPB, DCDPA, 2, 8-bis (9-phenyl-9H-carbazol-3-yl) dibenzo [ b, d ] thiophene and/or 3, 6-bis (N-carbazolyl) -N-phenyl-carbazole.

HBL 21150 may include but is not limited to based onOxadiazole-based compound, triazole-based compound, phenanthroline-based compound, and benzo-based compoundAzole compounds, benzothiazole-based compounds, benzimidazole-based compounds, triazine-based compounds, and the like.

The CGL 11070 is disposed between the first and second light emitting portions 1000 and 1100, and the CGL 21170 is disposed between the second and third light emitting portions 1100 and 1200. Each of the CGLs 11070 and 21170 may be a PN junction CGL including a first N-type CGL 1080 or a second N-type CGL 1180 and a first P-type CGL 1090 or a second P-type CGL 1190. The CGL 11070 includes a first N-type CGL 1080 disposed adjacent to the first light emitting part 1000 and a first P-type CGL 1090 disposed adjacent to the second light emitting part 1100. CGL 21170 includes a second N-type CGL 1180 provided adjacent to second light emitting unit 1100 and a second P-type CGL 1190 provided adjacent to third light emitting unit 1200. Each of the first and second N-type CGLs 1080 and 1180 injects electrons to each of the first and second light emitting parts 1000 and 1100, respectively, and each of the first and second P-type CGLs 1090 and 1190 injects holes to each of the second and third light emitting parts 1100 and 1200, respectively.

The OLED D4 according to the third embodiment of the present disclosure may improve its light emitting efficiency and may improve its light emitting life by: each of the first body 1042 and the first body 1242 of the anthracene-based compound having the structures of formula 1 to formula 2 and each of the first dopant 1044 and the first dopant 1244 of the boron-based compound having the structures of formula 3 to formula 4 are applied to each of the EML 11040 and the EML 31240, respectively, the arylamine-based compound having the structures of formula 5 and formula 6 is applied to each of the EBL 11030 and the EBL 31230, respectively, optionally the oxazine-based compound having the structures of formula 7 to formula 8 and/or the benzimidazole-based compound having the structures of formula 9 to formula 10 is applied to each of the HBL 11050 and the HBL 31250, respectively, and the red-green or yellow-green fluorescent material is applied to the EML 21140, respectively. In particular, the OLED D4 includes a three-stack structure in which two light emitting parts each emitting blue (B) light, i.e., a light emitting part 1000 and a light emitting part 1200, and one light emitting part 1100 emitting red-green (RG) light or yellow-green (YG) light are laminated, so that the organic light emitting display device 600 (see fig. 5) can emit white light (W).

In fig. 7, an OLED D4 of a serial structure in which three light emitting sections are laminated is shown. Alternatively, the OLED may further include at least one additional light emitting part and at least one additional charge generation layer.

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

As shown in fig. 8, the organic light emitting display device 1300 includes: a first substrate 1302 defining each of red, green and blue pixels RP, GP and BP; a second substrate 1304 facing the first substrate 1302; a thin film transistor Tr over the first substrate 1302; an Organic Light Emitting Diode (OLED) D disposed between the first and second substrates 1302 and 1304 and emitting blue (B) light; and a color conversion layer 1380 disposed between the OLED D and the second substrate 1304. Although not shown in fig. 8, a color filter layer may be disposed between the second substrate 1304 and each color conversion layer 1380.

The thin film transistor Tr is disposed over the first substrate 1302 corresponding to each of the red, green, and blue pixels RP, GP, and BP. A passivation layer 1360 is formed over the entire first electrode 1302 and covers the thin film transistor, the passivation layer 1360 having a drain contact hole exposing one electrode, for example, a drain electrode, constituting the thin film transistor Tr.

An OLED D including a first electrode 1410, a light emitting layer 1430, and a second electrode 1420 is disposed over the passivation layer 1360. The first electrode 1410 may be connected to a drain electrode of the thin film transistor Tr through a drain contact hole. Further, a bank layer 1364 covering an edge of the first electrode 1410 is formed at a boundary between the red pixel RP, the green pixel GP, and the blue pixel BP. In this case, the OLED D may have the structure of fig. 3 or 4, and may emit blue (B) light. The OLED D is disposed in each of the red, green, and blue pixels RP, GP, and BP to provide blue (B) light.

The color conversion layer 1380 may include a first color conversion layer 1382 corresponding to the red pixel RP and a second color conversion layer 1384 corresponding to the green pixel GP. For example, the color conversion layer 1380 may contain inorganic luminescent materials such as Quantum Dots (QDs).

Blue (B) light emitted from the OLED D in the red pixel RP is converted into red (R) light by the first color conversion layer 1382, and blue (B) light emitted from the OLED D in the green pixel GP is converted into green (G) light by the second color conversion layer 1384. Accordingly, the organic light emitting display device 1300 may implement a color image.

In addition, when light emitted from the OLED D is displayed through the first substrate 1302, a color conversion layer 1380 may be disposed between the OLED D and the first substrate 1302.

Synthesis example 1: synthesis of the body 1

(1) Synthesis of intermediate H-1

[ reaction formula 1-1]

Anhydrous copper bromide (45g, 0.202mol) was added to CCl dissolved with anthracene-D10 (18.8g, 0.10mol)₄In solution. The mixture was heated and stirred under nitrogen atmosphere for 12 hours. After completion of the reaction, the white cubr (i) compound was filtered off and the filtrate was purified by passing through a 35nm alumina column. The solvent was removed from the reaction solution purified by the column under vacuum to obtain a mixture containing intermediate H-1 (9-bromoanthracene-D9). The mixture comprised intermediate H-1, starting material (anthracene-D10), and dibromo byproduct. The mixture, which was not further purified, was used as starting material in equation 1-2.

(2) Synthesis of intermediate H-2

[ reaction formulae 1-2]

Intermediate H-1(2.66g, 0.01mol) and naphthalene-1-boronic acid (1.72g, 0.01mol) were added to a round-bottom flask, and then toluene (30ml) was added to the flask to form a mixture solution. Stirring a mixture solution to which Na is added under a nitrogen atmosphere₂CO₃(2.12g) Na dissolved in distilled water (10ml)₂CO₃An aqueous solution. Pd (PPh) was additionally added as a catalyst₃)₄(0.25g, 0.025mmol) and stirred. After completion of the reaction, the reaction solution was added to a methanol solution to precipitate a product, and the precipitated product was filtered. In the reduced-pressure filter, the precipitated product was washed sequentially with water, aqueous hydrogen chloride solution (10% concentration), water and methanol. The precipitated product was purified to obtain intermediate H-2(2.6g) as a white powder.

(3) Synthesis of intermediate H-3

[ reaction formulae 1 to 3]

After intermediate H-2(2.8g, 8.75mmol) was dissolved in dichloromethane (50 m)After L), Br is added to the solution₂(1.4g, 8.75mmol) and the solution was then stirred at Room Temperature (RT). After the reaction was complete, 2M Na was added to the reaction mass₂S₂O₃Aqueous solution (10ml) and stirred. The organic layer was separated and Na was used₂S₂O₃The aqueous solution (10% strength, 10ml) was washed with distilled water. The organic layer was separated again and purified by using MgSO₄The organic layer was freed of water. After the organic layer was concentrated, an excess of methanol was added to obtain a product. The product was filtered to give intermediate H-3(3.3 g).

(4) Synthesis of the body 1

[ reaction formulae 1 to 4]

Intermediate H-3(1.96g, 0.05mol) and naphthalene-2-boronic acid (1.02g, 0.06mol) were added and dissolved in toluene (30 ml). The mixture solution was stirred under a nitrogen atmosphere. Adding Na to the mixture solution₂CO₃(1.90g) Na dissolved in distilled water (8ml)₂CO₃Aqueous solution (1 ml). Pd (PPh) was additionally added₃)₄(0.125g, 0.0125 mmol). The mixture solution was heated and stirred under nitrogen atmosphere. After completion of the reaction, the organic layer was separated, and methanol was added to the organic layer to precipitate a white solid mixture. The white solid mixture was purified by silica gel column chromatography using an eluent of chloroform and hexane (volume ratio ═ 1:3) to give a main body 1(2.30 g).

Synthesis example 2: synthesis of the body 2

[ reaction formula 2]

Intermediate H-3(1.96g, 0.05mol) and 4- (naphthalen-2-yl) phenylboronic acid (1.49g, 0.06mol) were added and dissolved in toluene (30 ml). The mixture solution was stirred under a nitrogen atmosphere. Into the mixture solutionAdding Na₂CO₃(1.90g) Na dissolved in distilled water (8ml)₂CO₃Aqueous solution (1 ml). Pd (PPh) was additionally added₃)₄(0.125g, 0.0125 mmol). The mixture solution was heated and stirred under nitrogen atmosphere. After completion of the reaction, the organic layer was separated, and methanol was added to the organic layer to precipitate a white solid mixture. The white solid mixture was purified by silica gel column chromatography using an eluent of chloroform and hexane (volume ratio ═ 1:3) to give a body 2(2.30 g).

Synthesis example 3: synthesis of dopant 11-2

(1) Synthesis of intermediates I-P

[ reaction formula 3-1]

Under a nitrogen atmosphere, 2, 3-dichlorobromobenzene-D (22.0g), compound (I-E) (26.6g), bis (dibenzylideneacetone) palladium (0) (Pd (dba)₂2.68g), NaOtBu (16.8g), tri-tert-butylphosphine tetrafluoroborate (tBu)₃PHBF₄2.70g) and xylene (300ml) were placed in the flask, and then the mixed solution was heated at 120 ℃ 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 over a short column of silica gel (eluent: toluene/heptane 1/1 (vol.%)) to give intermediate (I-P) (35.0 g).

(2) Synthesis of intermediates I-Q

[ reaction formula 3-2]

Intermediate (I-P) (15.0g), intermediate (1-E) (8.4g), Pd-132 (bis [ di-t-butyl (4-dimethylaminophenyl) phosphine ] palladium, 0.21g) as a palladium catalyst, NaOtBu (4.3g), and xylene (60ml) were placed in a flask under a nitrogen atmosphere, and the mixed solution was heated at 120 ℃ 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 by means of a silica short column (eluent: toluene) to obtain intermediate (I-Q) (14.6 g).

(3) Synthesis of dopant 11-2

[ reaction formula 3-3]

To a flask containing intermediate (I-Q) (14.6g) and tert-butyl benzene (120ml) was added dropwise a 1.56M solution of tert-butyl lithium in pentane (27.5ml) at 0 ℃ under a nitrogen atmosphere. After the dropwise addition of the tert-butyllithium solution in pentane was completed, the temperature of the mixture was raised to 70 ℃, and then the mixture was stirred for 0.5 hour. The residue was cooled to-50 ℃, boron tribromide (10.7g) 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 ℃, to which was added N, N-diisopropylethylamine (EtNiPr)₂5.5g), and the mixture was stirred at room temperature until heat generation ended. Subsequently, the temperature of the mixture was raised to 100 ℃, and stirred and heated for 1 hour. The reaction solution was cooled to room temperature, a cooled aqueous sodium acetate solution and then ethyl acetate were added thereto, and the mixture was separated into layers. The organic layer was concentrated and then purified with a short column of silica gel (eluent: toluene). The crude product obtained was reprecipitated from heptane. Thus, compound dopant 11-2(0.5g) was obtained.

Synthesis example 4: synthesis of dopant 11-3

(1) Synthesis of intermediates I-F

[ reaction formula 4-1]

Under a nitrogen atmosphere, 2, 3-dichlorobromobenzene (22.0g), compound (I-E) (26.6g), (Pd (dba)₂(2.68g)、NaOtBu(16.8g)、tBu₃PHBF₄(2.70g) and xylene (300ml) were placed in the flask, and the mixed solution was heated at 120 ℃ 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 over a short column of silica gel (eluent: toluene/heptane 1/1 (vol.%)) to afford intermediate (I-F) (38.0 g).

(2) Synthesis of intermediates I-G

[ reaction formula 4-2]

Intermediate (I-F) (15.0g), intermediate (1-E) (8.4g), Pd-132(0.21g) as a palladium catalyst, NaOtBu (4.3g) and xylene (60ml) were placed in a flask under a nitrogen atmosphere, and the mixed solution was heated at 120 ℃ 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 by means of a silica short column (eluent: toluene) to obtain intermediate (I-G) (15.0G).

(3) Synthesis of dopant 11-3

[ reaction formula 4-3]

To a flask containing intermediate (I-G) (15.0G) and tert-butyl benzene (120ml) was added dropwise a 1.56M solution of tert-butyllithium in pentane (27.5ml) at 0 ℃ under a nitrogen atmosphere. After the dropwise addition of the tert-butyllithium solution in pentane was completed, the temperature of the mixture was raised to 70 ℃, and then the mixture was stirred for 0.5 hour. The residue was cooled to-50 ℃, boron tribromide (10.7g) was added thereto, and mixing was performedThe temperature of the material was raised to room temperature, and then the mixture was stirred for 0.5 hour. Thereafter, the mixture was cooled again to 0 ℃, to which EtNiPr was added₂(5.5g), and the mixture was stirred at room temperature until heat generation ended. Subsequently, the temperature of the mixture was raised to 100 ℃, and stirred and heated for 1 hour. The reaction solution was cooled to room temperature, a cooled aqueous sodium acetate solution and then ethyl acetate were added thereto, and the mixture was separated into layers. The organic layer was concentrated and then purified with a short column of silica gel (eluent: toluene). The crude product obtained was reprecipitated from heptane. Thus, compound dopant 11-3(6.5g) was obtained.

Synthesis example 5: synthesis of dopant 11-4

(1) Synthesis of intermediates I-S

[ reaction formula 5-1]

Under a nitrogen atmosphere, 2, 3-dichlorobromobenzene-D (22.0g), compound (I-R) (26.6g), (Pd (dba))₂(2.68g)、NaOtBu(16.8g)、tBu₃PHBF₄(2.70g) and xylene (300ml) were placed in the flask, and the mixed solution was heated at 120 ℃ 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 over a short column of silica gel (eluent: toluene/heptane 1/1 (vol.%)) to give intermediate (I-S) (38.0 g).

(2) Synthesis of intermediates I-T

[ reaction formula 5-2]

Intermediate (I-S) (15.0g), intermediate (I-R) (8.4g), Pd-132(0.21g) as a palladium catalyst, NaOtBu (4.3g) and xylene (60ml) were placed in a flask under a nitrogen atmosphere, and the mixed solution was heated at 120 ℃ 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 by means of a silica short column (eluent: toluene) to obtain intermediate (I-T) (15.0 g).

(3) Synthesis of dopant 11-4

[ reaction formulae 5-3]

To a flask containing intermediate (I-T) (15.0g) and tert-butyl benzene (120ml) was added dropwise a 1.56M solution of tert-butyllithium in pentane (27.5ml) at 0 ℃ under a nitrogen atmosphere. After the dropwise addition of the tert-butyllithium solution in pentane was completed, the temperature of the mixture was raised to 70 ℃, and then the mixture was stirred for 0.5 hour. The residue was cooled to-50 ℃, boron tribromide (10.7g) 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 ℃, to which EtNiPr was added₂(5.5g), and the mixture was stirred at room temperature until heat generation ended. Subsequently, the temperature of the mixture was raised to 100 ℃, and stirred and heated for 1 hour. The reaction solution was cooled to room temperature, a cooled aqueous sodium acetate solution and then ethyl acetate were added thereto, and the mixture was separated into layers. The organic layer was concentrated and then purified with a short column of silica gel (eluent: toluene). The crude product obtained was reprecipitated from heptane. Thus, compound dopant 11-4(8.0g) was obtained.

Synthesis example 6: synthesis of dopant 11-1

(1) Synthesis of intermediate I-5

[ reaction formula 6-1]

Under the nitrogen atmosphere, the reaction kettle is filled with nitrogen,2, 3-dichlorobromobenzene (22.0g), bis (4-tert-butylphenyl) amine (26.6g), Pd (dba)₂(2.68g)、NaOtBu(16.8g)、tBu₃PHBF₄(2.70g) and xylene (300ml) were placed in the flask, and the mixed solution was heated at 120 ℃ 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 over a short column of silica gel (eluent: toluene/heptane 1/1 (vol.%)) to give intermediate (I-5) (38.0 g).

(2) Synthesis of intermediate I-6

[ reaction formula 6-2]

Intermediate (I-5) (15.0g), bis (4-tert-butylphenyl) amine (8.4g), Pd-132(0.21g) as a palladium catalyst, NaOtBu (4.3g) and xylene (60ml) were placed in a flask under a nitrogen atmosphere, and the mixed solution was heated at 120 ℃ 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 by means of a silica short column (eluent: toluene) to obtain intermediate (I-6) (15.0 g).

(3) Synthesis of dopant 11-1

[ reaction formula 6-3]

To a flask containing intermediate (I-6) (15.0g) and tert-butyl benzene (120ml) was added dropwise a 1.56M pentane solution of tert-butyl lithium (27.5ml) at 0 ℃ under a nitrogen atmosphere. After the dropwise addition of the tert-butyllithium solution in pentane was completed, the temperature of the mixture was raised to 70 ℃, and then the mixture was stirred for 0.5 hour. The residue was cooled to-50 ℃, boron tribromide (10.7g) was added thereto, and the temperature of the mixture was raisedTo room temperature, the mixture was then stirred for 0.5 h. Thereafter, the mixture was cooled again to 0 ℃, to which EtNiPr was added₂(5.5g), and the mixture was stirred at room temperature until heat generation ended. Subsequently, the temperature of the mixture was raised to 100 ℃, and stirred and heated for 1 hour. The reaction solution was cooled to room temperature, a cooled aqueous sodium acetate solution and then ethyl acetate were added thereto, and the mixture was separated into layers. The organic layer was concentrated and then purified with a short column of silica gel (eluent: toluene). The crude product obtained was reprecipitated from heptane. Thus, compound dopant 11-1(6.5g) was obtained.

Synthesis example 7: synthesis of dopant 21-2

(1) Synthesis of intermediates I-N

[ reaction formula 7-1]

Intermediate (I-M) (22.5g), 4-bromo-tert-butylbenzene-D4 (17.0g), Pd-132(0.57g), NaOtBu (11.5g) and xylene (150ml) were placed in a flask under a nitrogen atmosphere, and the mixed solution was heated and stirred 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 over a short column of silica gel (eluent: toluene/heptane 2/8 (vol.%)) to give intermediate (I-N) (30.0 g).

(2) Synthesis of intermediates I-O

[ reaction formula 7-2]

Intermediate (I-C) (12.0g), intermediate (I-N) (10.7g), Pd-132(0.19g), NaOtBu (3.9g) and xylene (60ml) were placed in a flask under a nitrogen atmosphere, and the mixed solution was heated at 120 ℃ for 1.5 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 twice with water. Thereafter, the organic layer was concentrated to obtain a crude product. The crude product was purified over a short column of silica gel (eluent: toluene/heptane 2/8 (vol.%)) to give intermediate (I-O) (18.0 g).

(3) Synthesis of dopant 21-2

[ reaction formula 7-3]

To a flask containing intermediate (I-O) (18.0g) and tert-butyl benzene (90ml) was added dropwise a 1.62M pentane solution of tert-butyl lithium (40.0ml) at 0 ℃ under a nitrogen atmosphere. After the dropwise addition of the tert-butyllithium solution in pentane was completed, the temperature of the mixture was raised to 60 ℃, and then the mixture was stirred for 1 hour. The residue was cooled to-50 ℃, boron tribromide (16.5g) 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 ℃, to which EtNiPr was added₂(5.7g), and the mixture was stirred at 100 ℃ for 1 hour. After the reaction, an aqueous sodium acetate solution was added to the reaction solvent, the mixture was stirred, ethyl acetate was added to the mixture, and then the mixture was stirred again. The organic layer was separated to obtain a crude product, which was then purified by silica gel column chromatography (eluent: toluene/heptane 3/7 (volume ratio)) to obtain dopant 21-2(0.6 g).

Synthesis example 8: synthesis of dopant 21-3

(1) Synthesis of intermediate I-B

[ reaction formula 8-1]

Intermediate (I-A) (22.5g), 4-bromo-tert-butylbenzene (17.0g), Pd-132(0.57g), NaOtBu (11.5g) and xylene (150ml) were placed in a flask under a nitrogen atmosphere, and the mixed solution was heated and stirred 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 twice with water. Thereafter, the organic layer was concentrated to obtain a crude product. The crude product was purified over a short column of silica gel (eluent: toluene/heptane 2/8 (vol.%)) to give intermediate (I-B) (31.0 g).

(2) Synthesis of intermediates I-D

[ reaction formula 8-2]

Intermediate (I-C) (12.0g), intermediate (I-B) (10.7g), Pd-132(0.19g), NaOtBu (3.9g) and xylene (60ml) were placed in a flask under a nitrogen atmosphere, and the mixed solution was heated at 120 ℃ 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 twice with water. Thereafter, the organic layer was concentrated to obtain a crude product. The crude product was purified over a short column of silica gel (eluent: toluene/heptane 2/8 (vol.%)) to give intermediate (I-D) (19.9 g).

(3) Synthesis of dopant 21-3

[ reaction formula 8-3]

To a flask containing intermediate (I-D) (18.0g) and tert-butyl benzene (90ml) was added dropwise a 1.62M solution of tert-butyl lithium in pentane (40.0ml) at 0 ℃ under a nitrogen atmosphere. After the dropwise addition of the tert-butyllithium solution in pentane was completed, the temperature of the mixture was raised to 60 ℃, and then the mixture was stirred for 1 hour. The components having a boiling point lower than that of tert-butylbenzene were distilled under reduced pressure. The residue was cooled to-50 ℃, boron tribromide (16.5g) 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 ℃, to which EtNiPr was added₂(5.7g) andthe mixture was stirred at 100 ℃ for 1 hour. After the reaction, an aqueous sodium acetate solution was added to the reaction solvent, the mixture was stirred, ethyl acetate was added to the mixture, and then the mixture was stirred again. The organic layer was separated to obtain a crude product, which was then purified by silica gel column chromatography (eluent: toluene/heptane-3/7 (volume ratio)) to obtain dopant 21-3(4.0 g).

Synthesis example 9: synthesis of dopant 21-4

(1) Synthesis of intermediates I-J

[ reaction formula 9-1]

Intermediate (I-A) (22.5g), 4-bromo-tert-butylbenzene-D4 (17.0g), Pd-132(0.57g), NaOtBu (11.5g) and xylene (150ml) were placed in a flask under a nitrogen atmosphere, and the mixed solution was heated and stirred 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 twice with water. Thereafter, the organic layer was concentrated to obtain a crude product. The crude product was purified over a short column of silica gel (eluent: toluene/heptane 2/8 (vol.%)) to give intermediate (I-J) (31.0 g).

(2) Synthesis of intermediates I-L

[ reaction formula 9-2]

Intermediate (I-K) (12.0g), intermediate (I-J) (10.7g), Pd-132(0.19g), NaOtBu (3.9g) and xylene (60ml) were placed in a flask under a nitrogen atmosphere, and the mixed solution was heated at 120 ℃ 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 twice with water. Thereafter, the organic layer was concentrated to obtain a crude product. The crude product was purified over a short column of silica gel (eluent: toluene/heptane 2/8 (vol.%)) to give intermediate (I-L) (19.9 g).

(3) Synthesis of dopant 21-4

[ reaction formula 9-3]

To a flask containing intermediate (I-L) (18.0g) and tert-butyl benzene (90ml) was added dropwise a 1.62M pentane solution of tert-butyl lithium (40.0ml) at 0 ℃ under a nitrogen atmosphere. After the dropwise addition of the tert-butyllithium solution in pentane was completed, the temperature of the mixture was raised to 60 ℃, and then the mixture was stirred for 1 hour. The components having a boiling point lower than that of tert-butylbenzene were distilled under reduced pressure. The residue was cooled to-50 ℃, boron tribromide (16.5g) 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 ℃, to which EtNiPr was added₂(5.7g), and the mixture was stirred at 100 ℃ for 1 hour. After the reaction, an aqueous sodium acetate solution was added to the reaction solvent, the mixture was stirred, ethyl acetate was added to the mixture, and then the mixture was stirred again. The organic layer was separated to obtain a crude product, which was then purified by silica gel column chromatography (eluent: toluene/heptane-3/7 (volume ratio)) to obtain dopant 21-4(4.0 g).

Synthesis example 10: synthesis of dopant 21-1

(1) Synthesis of intermediate I-2

[ reaction formula 10-1]

Intermediate (I-1) (22.5g), 4-bromo-tert-butylbenzene (17.0g), Pd-132(0.57g), NaOtBu (11.5g) and xylene (150ml) were placed in a flask under a nitrogen atmosphere, and the mixed solution was heated and stirred 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 twice with water. Thereafter, the organic layer was concentrated to obtain a crude product. The crude product was purified over a short column of silica gel (eluent: toluene/heptane 2/8 (vol.%)) to give intermediate (I-2) (31.0 g).

(2) Synthesis of intermediate I-4

[ reaction formula 10-2]

Intermediate (I-3) (12.0g), intermediate (I-2) (10.7g), Pd-132(0.19g), NaOtBu (3.9g) and xylene (60ml) were placed in a flask under a nitrogen atmosphere, and the mixed solution was heated at 120 ℃ 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 twice with water. Thereafter, the organic layer was concentrated to obtain a crude product. The crude product was purified over a short column of silica gel (eluent: toluene/heptane 2/8 (vol.%)) to give intermediate (I-4) (19.9 g).

(3) Synthesis of dopant 21-1

[ reaction formula 10-3]

To a flask containing intermediate (I-4) (18.0g) and tert-butyl benzene (90ml) was added dropwise a 1.62M pentane solution of tert-butyl lithium (40.0ml) at 0 ℃ under a nitrogen atmosphere. After the dropwise addition of the tert-butyllithium solution in pentane was completed, the temperature of the mixture was raised to 60 ℃, and then the mixture was stirred for 1 hour. The components having a boiling point lower than that of tert-butylbenzene were distilled under reduced pressure. The residue was cooled to-50 ℃, boron tribromide (16.5g) 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 ℃, to which EtNiPr was added₂(5.7g), and the mixture was stirred at 100 ℃ for 1 hour. After the reaction, an aqueous solution of sodium acetate was added to the reaction solvent, the mixture was stirred, and acetic acid was added to the mixtureEthyl ester and then the mixture was stirred again. The organic layer was separated to obtain a crude product, which was then purified by silica gel column chromatography (eluent: toluene/heptane-3/7 (volume ratio)) to obtain dopant 21-1(4.0 g).

Example 1 (ex.1): manufacture of Organic Light Emitting Diodes (OLEDs)

An organic light emitting diode is manufactured by: the host 1 synthesized in synthesis example 1 as a host and the dopant 21-2 synthesized in synthesis example 7 as a dopant were applied to the light Emitting Material Layer (EML), the E5 in formula 6 was applied to the Electron Blocking Layer (EBL), and 2-phenyl-9, 10-bis (2, 2' -bipyridin-5-yl) anthracene was applied to the Hole Blocking Layer (HBL). The glass substrate (40mm × 40mm × 40mm) on which ITO was coated as a thin film was washed and ultrasonically cleaned by a solvent (e.g., isopropyl alcohol, acetone, and distilled water) for 5 minutes, and dried in an oven at 100 ℃. After cleaning the substrate, O is used under vacuum₂The substrate was plasma treated for 2 minutes and then transferred to a vacuum chamber for deposition of a light emitting layer. Then, in the following order, at about 10^-7The luminescent layer and cathode were deposited by evaporation from a heated boat:

a Hole Injection Layer (HIL) (formula 11(97 wt%) and formula 12(3 wt%),) (ii) a A Hole Transport Layer (HTL) (formula 12,) (ii) a The EBL (E5 in equation 6,) (ii) a EML (host 1(98 wt.%) and dopant 21-2(2 wt.%),) (ii) a HBL (2-phenyl-9, 10-bis (2, 2' -bipyridin-5-yl) anthracene),) (ii) a Electronic deviceAn injection layer (EIL) (1, 3-bis (9-phenyl-1, 10-phenanthrolin-2-yl) benzene (98 wt%) and Li (2 wt%),) (ii) a And a cathode (Al,)。

a capping layer (CPL) is then deposited over the cathode and passed through a glass encapsulation device. After deposition of the light emitting layer and the cathode, the OLED was transferred from the deposition chamber into a dry box for film formation and then encapsulated with UV curable epoxy and moisture absorber.

[ formula 11]

[ formula 12]

Examples 2 to 3(ex.2 to 3): fabrication of OLEDs

An OLED was manufactured 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 HBL.

Comparative examples 1 to 3(ref.1 to 3): fabrication of OLEDs

An OLED was manufactured using the same process and the same material as each of examples 1 to 3, except that host 1-1 in the following formula 13 was used as a host in the EML and NPB (N, N '-di (1-naphthyl) -N, N' -diphenyl- (1,1 '-biphenyl) -4, 4' -diamine) was used as a material in the EBL, respectively.

Comparative examples 4 to 6(ref.4 to 6): fabrication of OLEDs

An OLED was manufactured using the same process and the same material as each of examples 1 to 3, except that the host 1-2 in the following formula 13 was used as a host in an EML and NPB was used as a material in an EBL, respectively.

Comparative examples 7 to 9 (Ref.7-9): fabrication of OLEDs

OLEDs were manufactured using the same process and the same materials as each of examples 1 to 3, except that NPB was used as the material in the EBL, respectively.

Comparative examples 10 to 12(ref.10 to 12): fabrication of OLEDs

An OLED was manufactured using the same process and the same material as each of examples 1 to 3, except that hosts 1 to 3 in the following formula 13 were used as hosts in the EML and NPB was used as a material in the EBL, respectively.

Comparative examples 13 to 15(ref.13 to 15): fabrication of OLEDs

An OLED was manufactured using the same process and the same material as each of examples 1 to 3, except that hosts 1 to 4 in the following formula 13 were used as hosts in the EML and NPB was used as a material in the EBL, respectively.

[ formula 13]

Experimental example 1: measurement of the luminescence characteristics of OLEDs

The light emitting areas manufactured in examples 1 to 3 and comparative examples 1 to 15 were 9mm²Each of the OLEDs of (a) is connected to an external power source, and then the light emission characteristics of all the OLEDs are evaluated at room temperature using a constant current source (KEITHLEY) and a photometer PR 650. In particular at 10mA/cm²Current density (V), current efficiency (Cd/A) and color coordinates, and at 40 ℃ and 22.5mA/cm²A period of time (T) during which the luminance decreases from the initial luminance at 3000 nits to 95% at the current density of (1)₉₅). The measurement results are shown in table 1 below.

Table 1: luminescence characteristics of OLEDs

As shown in table 1, the OLEDs manufactured in comparative examples 7 to 9 using host 1 whose anthracene nucleus is deuterated in the EML exhibited significantly increased emission lifetimes as compared to the OLEDs in comparative examples 1 to 3 using host 1-1 that is not deuterated in the EML or the OLEDs in comparative examples 4 to 6 and comparative examples 10 to 12 using host 1-2 or host 1-3 whose anthracene substituent is deuterated in the EML. In addition, the OLEDs manufactured in comparative examples 7 to 9 using the host 1 in the EML showed improved current efficiency and emission lifetime, compared to the OLEDs manufactured in comparative examples 13 to 15 using the host 1-4 in the EML in which both the anthracene nucleus and the substituent are deuterated. Such results indicate that sufficient luminous efficiency and increased lifetime can be achieved with less expensive deuterium.

In addition, the OLEDs manufactured in examples 1 to 3 using E5 of formula 6 in the EBL improved their current efficiency and emission lifetime by as much as 85.7% and 196.5%, respectively, compared to the OLEDs manufactured in comparative examples 7 to 9 using NPB in the EBL. In particular, when the OLED includes H1 of formula 8 or H31 of formula 10 in the HBL, its current efficiency and light emitting lifetime are significantly improved.

Example 4 (ex.4): fabrication of OLEDs

An OLED was manufactured using the same procedure and the same material as in example 1, except that the dopant 21-2 was used as a dopant in the EML.

Examples 5 to 6(ex.5 to 6): fabrication of OLEDs

An OLED was manufactured 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 HBL.

Comparative examples 16 to 18(ref.16 to 18): fabrication of OLEDs

An OLED was manufactured using the same process and the same material as each of examples 4 to 6, except that the host 1-1 in formula 13 was used as a host in the EML and NPB was used as a material in the EBL, respectively.

Comparative examples 19 to 21(ref.19 to 21): fabrication of OLEDs

An OLED was manufactured using the same process and the same material as each of examples 4 to 6, except that the host 1-2 in formula 13 was used as a host in the EML and NPB was used as a material in the EBL, respectively.

Comparative examples 22 to 24(ref.22 to 24): fabrication of OLEDs

OLEDs were manufactured using the same procedure and the same materials as each of examples 4 to 6, except that NPB was used as the material in the EBL, respectively.

Comparative examples 25 to 27(ref.25 to 27): fabrication of OLEDs

An OLED was manufactured using the same process and the same material as each of examples 4 to 6, except that hosts 1 to 3 in formula 13 were used as hosts in the EML and NPB was used as a material in the EBL, respectively.

Comparative examples 28 to 30(ref.28 to 30): fabrication of OLEDs

An OLED was manufactured using the same process and the same material as each of examples 4 to 6, except that hosts 1 to 4 in formula 13 were used as hosts in the EML and NPB was used as a material in the EBL, respectively.

Experimental example 2: measurement of the luminescence characteristics of OLEDs

The light emission characteristics of each of the OLEDs manufactured in examples 4 to 6 and comparative examples 16 to 30 were measured using the same procedure as in experimental example 1. The measurement results are shown in table 2 below.

Table 2: luminescence characteristics of OLEDs

As shown in table 2, the OLEDs manufactured in comparative examples 22 to 24 using host 1 whose anthracene nucleus is deuterated in the EML exhibited significantly increased emission lifetimes as compared to the OLEDs in comparative examples 16 to 18 using host 1-1 that is not deuterated in the EML or the OLEDs in comparative examples 19 to 21 and comparative examples 25 to 27 using host 1-2 or host 1-3 whose anthracene substituent is deuterated in the EML. In addition, the OLEDs manufactured in comparative examples 22 to 24 using the host 1 in the EML exhibited comparable or slightly decreased current efficiency and light emission lifetime as compared to the OLEDs manufactured in comparative examples 28 to 30 using the host 1-4 in the EML in which both the anthracene nucleus and the substituent are deuterated. Such results indicate that sufficient luminous efficiency and increased lifetime can be achieved with less expensive deuterium.

In addition, the OLEDs manufactured in examples 4 to 6 using E5 of formula 6 in the EBL improved their current efficiency and emission lifetime by as much as 116.7% and 256.3%, respectively, compared to the OLEDs manufactured in comparative examples 22 to 24 using NPB in the EBL. In particular, when the OLED includes H1 of formula 8 or H31 of formula 10 in the HBL, its current efficiency and light emitting lifetime are significantly improved.

Example 7 (ex.7): fabrication of OLEDs

An OLED was manufactured using the same procedure and the same material as in example 1, except that the dopant 21-3 was used as a dopant in the EML.

Examples 8 to 9(ex.8 to 9): fabrication of OLEDs

An OLED was manufactured 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 HBL.

Comparative examples 31 to 33(ref.31 to 33): fabrication of OLEDs

An OLED was manufactured using the same procedure and the same material as each of examples 7 to 9, except that the host 1-1 in formula 13 was used as a host in the EML and NPB was used as a material in the EBL, respectively.

Comparative examples 34 to 36(ref.34 to 36): fabrication of OLEDs

An OLED was manufactured using the same procedure and the same material as each of examples 7 to 9, except that the host 1-2 in formula 13 was used as a host in the EML and NPB was used as a material in the EBL, respectively.

Comparative examples 37 to 39(ref.37 to 39): fabrication of OLEDs

OLEDs were manufactured using the same procedure and the same materials as each of examples 7 to 9, except that NPB was used as the material in the EBL, respectively.

Comparative examples 40 to 42(ref.40 to 42): fabrication of OLEDs

An OLED was manufactured using the same procedure and the same material as each of examples 7 to 9, except that hosts 1 to 3 in formula 13 were used as hosts in the EML and NPB was used as a material in the EBL, respectively.

Comparative examples 43 to 45(ref.43 to 45): fabrication of OLEDs

An OLED was manufactured using the same procedure and the same material as each of examples 7 to 9, except that hosts 1 to 4 in formula 13 were used as hosts in the EML and NPB was used as a material in the EBL, respectively.

Experimental example 3: measurement of the luminescence characteristics of OLEDs

The light emission characteristics of each of the OLEDs manufactured in examples 7 to 9 and comparative examples 31 to 45 were measured using the same procedure as in experimental example 1. The measurement results are shown in table 3 below.

Table 3: luminescence characteristics of OLEDs

As shown in table 3, the OLEDs manufactured in comparative examples 37 to 39 using host 1 whose anthracene nucleus is deuterated in the EML exhibited significantly increased emission lifetimes as compared to the OLEDs in comparative examples 31 to 33 using host 1-1 that is not deuterated in the EML or the OLEDs in comparative examples 34 to 36 and comparative examples 40 to 42 using host 1-2 or host 1-3 whose anthracene substituent of anthracene is deuterated in the EML. In addition, the OLEDs manufactured in comparative examples 37 to 39 using host 1 in the EML showed slightly improved current efficiency and slightly reduced emission lifetime, compared to the OLEDs manufactured in comparative examples 43 to 45 using host 1-4 in the EML in which both the anthracene nucleus and the substituent are deuterated. Such results indicate that sufficient luminous efficiency and increased lifetime can be achieved with less expensive deuterium.

In addition, the OLEDs manufactured in examples 7 to 9 using E5 of formula 6 in the EBL improved their current efficiency and emission lifetime by as much as 104.6% and 250%, respectively, compared to the OLEDs manufactured in comparative examples 37 to 39 using NPB in the EBL. In particular, when the OLED includes H1 of formula 8 or H31 of formula 10 in the HBL, its current efficiency and light emitting lifetime are significantly improved.

Example 10 (ex.10): fabrication of OLEDs

An OLED was manufactured using the same procedure and the same material as in example 1, except that the dopant 21-4 was used as a dopant in the EML.

Examples 11 to 12(ex.11 to 12): fabrication of OLEDs

An OLED was manufactured 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 HBL.

Comparative example46 to 48(Ref.46 to 48): fabrication of OLEDs

An OLED was manufactured using the same process and the same material as each of examples 10 to 12, except that the host 1-1 in formula 13 was used as the host in the EML and NPB was used as the material in the EBL, respectively.

Comparative examples 49 to 51(ref.49 to 51): fabrication of OLEDs

An OLED was manufactured using the same process and the same material as each of examples 10 to 12, except that the host 1-2 in formula 13 was used as a host in the EML and NPB was used as a material in the EBL, respectively.

Comparative examples 52 to 54(ref.52 to 54): fabrication of OLEDs

OLEDs were manufactured using the same procedure and the same materials as each of examples 10 to 12, except that NPB was used as the material in the EBL, respectively.

Comparative examples 55 to 57(ref.55 to 57): fabrication of OLEDs

An OLED was manufactured using the same process and the same material as each of examples 10 to 12, except that hosts 1 to 3 in formula 13 were used as hosts in the EML and NPB was used as a material in the EBL, respectively.

Comparative examples 58 to 60(ref.58 to 60): fabrication of OLEDs

An OLED was manufactured using the same process and the same material as each of examples 10 to 12, except that hosts 1 to 4 in formula 13 were used as hosts in the EML and NPB was used as a material in the EBL, respectively.

Experimental example 4: measurement of the luminescence characteristics of OLEDs

The light emission characteristics of each of the OLEDs manufactured in examples 10 to 12 and comparative examples 46 to 60 were measured using the same procedure as in experimental example 1. The measurement results are shown in table 4 below.

Table 4: luminescence characteristics of OLEDs

As shown in table 4, the OLEDs manufactured in comparative examples 52 to 54 using host 1 whose anthracene nucleus is deuterated in the EML exhibited significantly increased emission lifetimes as compared to the OLEDs in comparative examples 46 to 48 using host 1-1 that is not deuterated in the EML or the OLEDs in comparative examples 49 to 51 and comparative examples 55 to 57 using host 1-2 or host 1-3 whose anthracene substituent is deuterated in the EML. In addition, the OLEDs manufactured in comparative examples 52 to 54 using host 1 in the EML exhibited comparable or slightly decreased current efficiency and light emission lifetime as compared to the OLEDs manufactured in comparative examples 58 to 60 using host 1-4 in the EML in which the anthracene nucleus and the substituent are both deuterated. Such results indicate that sufficient luminous efficiency and increased lifetime can be achieved with less expensive deuterium.

In addition, the OLEDs manufactured in examples 10 to 12 using E5 of formula 6 in the EBL improved their current efficiency and emission lifetime by as much as 107.4% and 256.7%, respectively, compared to the OLEDs manufactured in comparative examples 52 to 54 using NPB in the EBL. In particular, when the OLED includes H1 of formula 8 or H31 of formula 10 in the HBL, its current efficiency and light emitting lifetime are significantly improved.

Example 13 (ex.13): fabrication of OLEDs

An OLED was manufactured using the same process and the same material as in example 1, except that the host 2 was used as a host in the EML.

Examples 14 to 15(ex.14 to 15): fabrication of OLEDs

An OLED was manufactured 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 HBL.

Comparative examples 61 to 63 (Ref.6)1 to 63): fabrication of OLEDs

An OLED was manufactured using the same procedure and the same material as each of examples 13 to 15, except that the host 2-1 in the following formula 14 was used as a host in the EML and NPB was used as a material in the EBL, respectively.

Comparative examples 64 to 66(ref.64 to 66): fabrication of OLEDs

An OLED was manufactured using the same procedure and the same material as each of examples 13 to 15, except that the host 2-2 in the following formula 14 was used as a host in the EML and NPB was used as a material in the EBL, respectively.

Comparative examples 67 to 69(ref.67 to 69): fabrication of OLEDs

OLEDs were manufactured using the same procedure and the same materials as each of examples 13 to 15, except that NPB was used as the material in the EBL, respectively.

Comparative examples 70 to 72(ref.70 to 72): fabrication of OLEDs

An OLED was manufactured using the same procedure and the same material as each of examples 13 to 15, except that hosts 2 to 3 in the following formula 14 were used as hosts in the EML and NPB was used as a material in the EBL, respectively.

Comparative examples 73 to 75(ref.73 to 75): fabrication of OLEDs

An OLED was manufactured using the same procedure and the same material as each of examples 13 to 15, except that hosts 2 to 4 in the following formula 14 were used as hosts in the EML and NPB was used as a material in the EBL, respectively.

[ formula 14]

Experimental example 5: measurement of the luminescence characteristics of OLEDs

The light emission characteristics of each of the OLEDs manufactured in examples 13 to 15 and comparative examples 61 to 75 were measured using the same procedure as in experimental example 1. The measurement results are shown in table 5 below.

Table 5: luminescence characteristics of OLEDs

As shown in table 5, the OLEDs manufactured in comparative examples 67 to 69 using host 2 whose anthracene nucleus is deuterated in the EML exhibited significantly increased emission lifetimes as compared to the OLEDs in comparative examples 61 to 63 using host 2-1 that is not deuterated in the EML or the OLEDs 64 to 66 and comparative examples 70 to 72 using host 2-2 or host 2-3 whose anthracene substituent group is deuterated in the EML. In addition, the OLEDs manufactured in comparative examples 67 to 69 using the host 2 in the EML exhibited comparable or slightly improved current efficiency and emission lifetime compared to the OLEDs manufactured in comparative examples 73 to 75 using the host 2-4 in the EML in which both the anthracene nucleus and the substituent are deuterated. Such results indicate that sufficient luminous efficiency and increased lifetime can be achieved with less expensive deuterium.

In addition, the OLEDs manufactured in examples 13 to 15 using E5 of formula 6 in the EBL improved their current efficiency and emission lifetime by as much as 107.4% and 201.2%, respectively, compared to the OLEDs manufactured in comparative examples 67 to 69 using NPB in the EBL. In particular, when the OLED includes H1 of formula 8 or H31 of formula 10 in the HBL, its current efficiency and light emitting lifetime are significantly improved.

Example 16 (ex.16): fabrication of OLEDs

An OLED was manufactured using the same procedure and the same material as in example 13, except that the dopant 21-2 was used as a dopant in the EML.

Examples 17 to 18(ex.17 to 18): fabrication of OLEDs

An OLED was manufactured 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 HBL.

Comparative examples 76 to 78(ref.76 to 78): fabrication of OLEDs

An OLED was manufactured using the same procedure and the same material as each of examples 16 to 18, except that the host 2-1 in formula 14 was used as the host in the EML and NPB was used as the material in the EBL, respectively.

Comparative examples 79 to 81(ref.79 to 81): fabrication of OLEDs

An OLED was manufactured using the same procedure and the same material as each of examples 16 to 18, except that the host 2-2 in formula 14 was used as the host in the EML and NPB was used as the material in the EBL, respectively.

Comparative examples 82 to 84(ref.82 to 84): fabrication of OLEDs

OLEDs were manufactured using the same procedure and the same materials as each of examples 16 to 18, except that NPB was used as the material in the EBL, respectively.

Comparative examples 85 to 87(ref.85 to 87): fabrication of OLEDs

An OLED was manufactured using the same procedure and the same materials as each of examples 16 to 18, except that the hosts 2 to 3 in formula 14 were used as hosts in the EML and NPB was used as a material in the EBL, respectively.

Comparative examples 88 to 90(ref.88 to 90): fabrication of OLEDs

An OLED was manufactured using the same procedure and the same materials as each of examples 16 to 18, except that the hosts 2 to 4 in formula 14 were used as hosts in the EML and NPB was used as a material in the EBL, respectively.

Experimental example 6: measurement of the luminescence characteristics of OLEDs

The light emission characteristics of each of the OLEDs manufactured in examples 16 to 18 and comparative examples 76 to 90 were measured using the same procedure as in experimental example 1. The measurement results are shown in table 6 below.

Table 6: luminescence characteristics of OLEDs

As shown in table 6, the OLEDs manufactured in comparative examples 82 to 84 using host 2 whose anthracene nucleus is deuterated in the EML exhibited significantly increased emission lifetimes as compared to the OLEDs in comparative examples 76 to 78 using host 2-1 that is not deuterated in the EML or the OLEDs in comparative examples 79 to 81 and comparative examples 85 to 87 using host 2-2 or host 2-3 whose anthracene substituent is deuterated in the EML. In addition, the OLEDs manufactured in comparative examples 82 to 84 using the host 2 in the EML exhibited comparable or slightly decreased current efficiency and light emission lifetime as compared to the OLEDs manufactured in comparative examples 88 to 90 using the host 2-4 in which both the anthracene nucleus and the substituent group are deuterated in the EML. Such results indicate that sufficient luminous efficiency and increased lifetime can be achieved with less expensive deuterium.

In addition, the OLEDs manufactured in examples 16 to 18 using E5 of formula 6 in the EBL improved their current efficiency and emission lifetime by as much as 103.7% and 250%, respectively, compared to the OLEDs manufactured in comparative examples 82 to 84 using NPB in the EBL. In particular, when the OLED includes H1 of formula 8 or H31 of formula 10 in the HBL, its current efficiency and light emitting lifetime are significantly improved.

Example 19 (ex.19): fabrication of OLEDs

An OLED was manufactured using the same procedure and the same material as in example 13, except that the dopant 21-3 was used as a dopant in the EML.

Examples 20 to 21(ex.20 to 21): fabrication of OLEDs

An OLED was manufactured 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 HBL.

Comparative examples 91 to 93(ref.91 to 93): fabrication of OLEDs

An OLED was manufactured using the same procedure and the same material as each of examples 19 to 21, except that the host 2-1 in formula 14 was used as the host in the EML and NPB was used as the material in the EBL, respectively.

Comparative examples 94 to 96(ref.94 to 96): fabrication of OLEDs

An OLED was manufactured using the same procedure and the same material as each of examples 19 to 21, except that the host 2-2 in formula 14 was used as the host in the EML and NPB was used as the material in the EBL, respectively.

Comparative examples 97 to 99(ref.97 to 99): fabrication of OLEDs

OLEDs were manufactured using the same procedure and the same materials as each of examples 19 to 21, except that NPB was used as the material in the EBL, respectively.

Comparative examples 100 to 102(ref.100 to 102): fabrication of OLEDs

An OLED was manufactured using the same procedure and the same material as each of examples 19 to 21, except that the hosts 2-3 in formula 14 were used as the hosts in the EML and NPB was used as the material in the EBL, respectively.

Comparative examples 103 to 105(ref.103 to 105): fabrication of OLEDs

An OLED was manufactured using the same procedure and the same material as each of examples 19 to 21, except that the hosts 2 to 4 in formula 14 were used as the hosts in the EML and NPB was used as the material in the EBL, respectively.

Experimental example 7: measurement of the luminescence characteristics of OLEDs

The light emission characteristics of each of the OLEDs manufactured in examples 19 to 21 and comparative examples 91 to 105 were measured using the same procedure as in experimental example 1. The measurement results are shown in table 7 below.

Table 7: luminescence characteristics of OLEDs

As shown in table 7, the OLEDs manufactured in comparative examples 97 to 99 using host 2 whose anthracene nucleus is deuterated in the EML exhibited significantly increased emission lifetimes as compared to the OLEDs in comparative examples 91 to 93 using host 2-1 that is not deuterated in the EML or the OLEDs in comparative examples 94 to 96 and comparative examples 100 to 102 using host 2-2 or host 2-3 whose anthracene substituent is deuterated in the EML. In addition, the OLEDs manufactured in comparative examples 97 to 99 using the host 2 in the EML exhibited comparable current efficiency and slightly reduced emission lifetime as compared to the OLEDs manufactured in comparative examples 103 to 105 using the host 2-4 in which both the anthracene nucleus and the substituent group are deuterated in the EML. Such results indicate that sufficient luminous efficiency and increased lifetime can be achieved with less expensive deuterium.

In addition, the OLEDs manufactured in examples 19 to 21 using E5 of formula 6 in the EBL improved their current efficiency and emission lifetime by as much as 106.1% and 229.1%, respectively, compared to the OLEDs manufactured in comparative examples 97 to 99 using NPB in the EBL. In particular, when the OLED includes H1 of formula 8 or H31 of formula 10 in the HBL, its current efficiency and light emitting lifetime are significantly improved.

Example 22 (ex.22): fabrication of OLEDs

An OLED was manufactured using the same procedure and the same material as in example 13, except that the dopant 21-4 was used as a dopant in the EML.

Examples 23 to 24(ex.23 to 24): fabrication of OLEDs

An OLED was manufactured 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 HBL.

Comparative examples 106 to 108(ref.106 to 108): fabrication of OLEDs

An OLED was manufactured using the same procedure and the same material as each of examples 22 to 24, except that the host 2-1 in formula 14 was used as the host in the EML and NPB was used as the material in the EBL, respectively.

Comparative examples 109 to 111(ref.109 to 111): fabrication of OLEDs

An OLED was manufactured using the same procedure and the same materials as each of examples 22 to 24, except that the host 2-2 in formula 14 was used as the host in the EML and NPB was used as the material in the EBL, respectively.

Comparative examples 112 to 114(ref.112 to 114): fabrication of OLEDs

OLEDs were manufactured using the same procedure and the same materials as each of examples 22 to 24, except that NPB was used as the material in the EBL, respectively.

Comparative examples 115 to 117(ref.115 to 117): fabrication of OLEDs

An OLED was manufactured using the same procedure and the same materials as each of examples 22 to 24, except that the hosts 2-3 in formula 14 were used as hosts in the EML and NPB was used as a material in the EBL, respectively.

Comparative examples 118 to 120(ref.118 to 120): fabrication of OLEDs

An OLED was manufactured using the same procedure and the same materials as each of examples 22 to 24, except that the hosts 2 to 4 in formula 14 were used as hosts in the EML and NPB was used as a material in the EBL, respectively.

Experimental example 8: measurement of the luminescence characteristics of OLEDs

The light emission characteristics of each of the OLEDs manufactured in examples 22 to 24 and comparative examples 106 to 120 were measured using the same procedure as in experimental example 1. The measurement results are shown in table 8 below.

Table 8: luminescence characteristics of OLEDs

As shown in table 8, the OLEDs manufactured in comparative examples 112 to 114 using host 2 whose anthracene nucleus is deuterated in the EML exhibited significantly increased emission lifetimes as compared to the OLEDs in comparative examples 106 to 108 using host 2-1 that is not deuterated in the EML or the OLEDs in comparative examples 109 to 111 and comparative examples 115 to 117 using host 2-2 or host 2-3 whose anthracene substituent is deuterated in the EML. In addition, the OLEDs manufactured in comparative examples 112 to 114 using the host 2 in the EML exhibited comparable or slightly decreased current efficiency and light emission lifetime as compared to the OLEDs manufactured in comparative examples 118 to 120 using the host 2-4 in the EML in which both the anthracene nucleus and the substituent group are deuterated. Such results indicate that sufficient luminous efficiency and increased lifetime can be achieved with less expensive deuterium.

In addition, the OLEDs manufactured in examples 22 to 24 using E5 of formula 6 in the EBL improved their current efficiency and emission lifetime by as much as 104.1% and 248.5%, respectively, compared to the OLEDs manufactured in comparative examples 112 to 114 using NPB in the EBL. In particular, when the OLED includes H1 of formula 8 or H31 of formula 10 in the HBL, its current efficiency and light emitting lifetime are significantly improved.

Example 25 (ex.25): fabrication of OLEDs

An OLED was manufactured using the same procedure and the same material as in example 1, except that the host 2 was used as a host in the EML and E9 in formula 6 was used as a material in the EBL.

Examples 26 to 27 (Ex.26)To 27): fabrication of OLEDs

An OLED was manufactured 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 HBL.

Example 28 (ex.28): fabrication of OLEDs

An OLED was manufactured using the same procedure and the same material as in example 25, except that the dopant 21-2 was used as a dopant in the EML.

Examples 29 to 30(ex.29 to 30): fabrication of OLEDs

An OLED was manufactured 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 HBL.

Example 31 (ex.31): fabrication of OLEDs

An OLED was manufactured using the same procedure and the same material as in example 25, except that the dopant 21-3 was used as a dopant in the EML.

Examples 32 to 33(ex.32 to 33): fabrication of OLEDs

An OLED was manufactured 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 HBL.

Example 34 (ex.34): fabrication of OLEDs

An OLED was manufactured using the same procedure and the same material as in example 25, except that the dopant 21-4 was used as a dopant in the EML.

Examples 35 to 36(ex.35 to 36): fabrication of OLEDs

An OLED was manufactured 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 HBL.

Experimental example 9: measurement of the luminescence characteristics of OLEDs

The light emission characteristics of each of the OLEDs manufactured in examples 25 to 36 and comparative examples 68 to 69, 83 to 84, 98 to 99, and 113 to 114 were measured using the same procedure as in experimental example 1. The measurement results are shown in table 9 below.

Table 9: luminescence characteristics of OLEDs

As shown in table 9, the OLEDs manufactured in examples 25 to 36 using E9 of formula 6 in the EBL improved their current efficiency and emission lifetime by as much as 122.3% and 238.6%, respectively, compared to the OLEDs manufactured in comparative examples 68 to 69, 83 to 84, 98 to 99, and 113 to 114 using NPB in the EBL. In particular, when the OLED includes H1 of formula 8 or H31 of formula 10 in the HBL, its current efficiency and light emitting lifetime are significantly improved.

Example 37 (ex.37): fabrication of OLEDs

An OLED was manufactured using the same process and the same material as in example 1, except that the host 2 was used as a host in the EML and the dopant 11-1 was used as a dopant in the EML.

Examples 38 to 39(ex.38 to 39): fabrication of OLEDs

An OLED was manufactured 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 HBL.

Comparative examples 121 to 122(ref.121 to 122): fabrication of OLEDs

OLEDs were manufactured using the same procedure and the same materials as each of examples 38 to 39, except that NPB was used as the material in the EBL, respectively.

Example 40 (ex.40): fabrication of OLEDs

An OLED was manufactured using the same procedure and the same material as in example 37, except that the dopant 11-2 was used as a dopant in the EML.

Examples 41 to 42(ex.41 to 42): fabrication of OLEDs

An OLED was manufactured 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 HBL.

Comparative examples 123 to 124(ref.123 to 124): fabrication of OLEDs

OLEDs were manufactured using the same procedure and the same materials as each of examples 41 to 42, except that NPB was used as the material in the EBL, respectively.

Example 43 (ex.43): fabrication of OLEDs

An OLED was manufactured using the same procedure and the same material as in example 37, except that the dopant 11-3 was used as a dopant in the EML.

Examples 44 to 45(ex.44 to 45): fabrication of OLEDs

An OLED was manufactured 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 HBL.

Comparative examples 125 to 126(ref.125 to 126): fabrication of OLEDs

OLEDs were manufactured using the same procedure and the same materials as each of examples 44 to 45, except that NPB was used as the material in the EBL, respectively.

Example 46 (ex.46): fabrication of OLEDs

An OLED was manufactured using the same procedure and the same material as in example 37, except that the dopant 11-4 was used as a dopant in the EML.

Examples 47 to 48(ex.47 to 48): fabrication of OLEDs

An OLED was manufactured 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 HBL.

Comparative examples 127 to 128(ref.127 to 128): fabrication of OLEDs

OLEDs were manufactured using the same procedure and the same materials as each of examples 47 to 48, except that NPB was used as the material in the EBL, respectively.

Experimental example 10: measurement of the luminescence characteristics of OLEDs

The light emission characteristics of each of the OLEDs manufactured in examples 37 to 48 and comparative examples 121 to 128 were measured using the same procedure as in experimental example 1. The measurement results are shown in table 10 below.

Table 10: luminescence characteristics of OLEDs

As shown in table 10, the OLEDs manufactured in examples 37 to 48 using E5 of formula 6 in the EBL improved their current efficiency and emission lifetime by as much as 105.6% and 250.8%, respectively, compared to the OLEDs manufactured in comparative examples 121 to 128 using NPB in the EBL. In particular, when the OLED includes H1 of formula 8 or H31 of formula 10 in the HBL, its current efficiency and light emitting lifetime are significantly improved.

Example 49 (ex.49): fabrication of OLEDs

An OLED was manufactured using the same procedure and the same materials as in example 1, except that host 2 was used as a host in the EML, dopant 11-1 was used as a dopant in the EML, and E9 was used as a material in the EBL.

Examples 50 to 51(ex.50 to 51): fabrication of OLEDs

An OLED was manufactured 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 HBL.

Comparative examples 129 to 130(ref.129 to 130): fabrication of OLEDs

OLEDs were manufactured using the same procedure and the same materials as each of examples 50 to 51, except that NPB was used as the material in the EBL, respectively.

Example 52 (ex.52): fabrication of OLEDs

An OLED was manufactured using the same procedure and the same material as in example 49, except that the dopant 11-2 was used as a dopant in the EML.

Examples 53 to 54(ex.53 to 54): fabrication of OLEDs

An OLED was manufactured 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 HBL.

Comparative examples 131 to 132(ref.131 to 132): fabrication of OLEDs

OLEDs were manufactured using the same procedure and the same materials as each of examples 53 to 54, except that NPB was used as the material in the EBL, respectively.

Example 55 (ex.55): fabrication of OLEDs

An OLED was manufactured using the same procedure and the same material as in example 49, except that the dopant 11-3 was used as a dopant in the EML.

Examples 56 to 57(ex.56 to 57): fabrication of OLEDs

An OLED was manufactured 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 HBL.

Comparative examples 133 to 134(ref.133 to 134): fabrication of OLEDs

OLEDs were manufactured using the same procedure and the same materials as each of examples 56 to 57, except that NPB was used as the material in the EBL, respectively.

Example 58 (ex.58): fabrication of OLEDs

An OLED was manufactured using the same procedure and the same material as in example 49, except that the dopant 11-4 was used as a dopant in the EML.

Examples 59 to 60(ex.59 to 60): fabrication of OLEDs

An OLED was manufactured 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 HBL.

Comparative examples 135 to 136(ref.135 to 136): fabrication of OLEDs

OLEDs were manufactured using the same procedure and the same materials as each of examples 59 to 60, except that NPB was used as the material in the EBL, respectively.

Experimental example 11: measurement of the luminescence characteristics of OLEDs

The light emission characteristics of each of the OLEDs manufactured in examples 49 to 60 and comparative examples 129 to 136 were measured using the same procedure as in experimental example 1. The measurement results are shown in table 11 below.

Table 11: luminescence characteristics of OLEDs

As shown in table 11, the OLEDs manufactured in examples 49 to 60 using E9 of formula 6 in the EBL improved their current efficiency and emission lifetime by as much as 122.8% and 237.0%, respectively, compared to the OLEDs manufactured in comparative examples 129 to 136 using NPB in the EBL. In particular, when the OLED includes H1 of formula 8 or H31 of formula 10 in the HBL, its current efficiency and light emitting lifetime are significantly improved.

It will be apparent to those skilled in the art that various modifications and variations can be made in the present disclosure without departing from the scope of the invention. Thus, it is intended that the present disclosure cover the modifications and variations of this disclosure provided they come within the scope of the appended claims.