OPTOELECTRONIC DEVICE AND ELECTRONIC APPARATUS INCLUDING THE SAME

Information

  • Patent Application
  • 20250241202
  • Publication Number
    20250241202
  • Date Filed
    January 17, 2025
    10 months ago
  • Date Published
    July 24, 2025
    4 months ago
  • CPC
    • H10K85/658
    • H10K85/615
    • H10K85/654
    • H10K85/6572
    • H10K85/6574
    • H10K30/20
    • H10K50/11
    • H10K50/16
  • International Classifications
    • H10K85/60
    • H10K30/20
    • H10K50/11
    • H10K50/16
Abstract
An optoelectronic device including a first electrode, a second electrode facing (e.g. opposite to) the first electrode, an optical activation layer arranged between the first electrode and the second electrode is provided. A buffer layer is arranged between the optical activation layer and the second electrode, wherein the optical activation layer may include a first compound represented by Formula 1 and a second compound represented by Formula 2, and the buffer layer may include a third compound represented by Formula 3.
Description
CROSS-REFERENCE TO RELATED APPLICATION

This application claims priority to and the benefit of Korean Patent Application No. 10-2024-0010149, filed on Jan. 23, 2024, in the Korean Intellectual Property Office, the entire content of which is incorporated herein by reference.


BACKGROUND
1. Field

One or more aspects of embodiments of the present disclosure relate to an optoelectronic device and an electronic apparatus including the same.


2. Description of the Related Art

Optoelectronic devices are devices that convert optical energy into electrical energy and/or optical energy or signals into electrical signals. Examples of an optoelectronic device are an optical or solar cell, which converts optical energy into electrical energy, an optical detector or sensor, which detects and converts optical energy or signals into electrical signals, and/or the like.


Electronic apparatuses including optoelectronic devices and light-emitting devices have been developed. Light emitted from a light-emitting device may be reflected from an object (e.g., a finger of a user) in contact with an electronic apparatus, and then incident on an optoelectronic device. As the optoelectronic device detects incident light energy and converts it into electrical signals, the contact of the object with the electronic apparatus may be recognized. The optoelectronic device may thus, e.g., be used as a fingerprint recognition sensor.


SUMMARY

One or more aspects of embodiments of the present disclosure are directed toward an optoelectronic device having excellent or suitable (e.g., high) external quantum efficiency and a high-quality electronic apparatus including the optoelectronic device.


Additional aspects will be set forth in part in the description which follows and, in part, will be apparent from the description, or may be learned by practice of the presented embodiments of the disclosure.


According to one or more embodiments, an optoelectronic device includes a first electrode, a second electrode facing (e.g. opposite to) the first electrode, an optical activation layer arranged between the first electrode and the second electrode, and a buffer layer arranged between the optical activation layer and the second electrode, wherein the optical activation layer may include a first compound represented by Formula 1 and a second compound represented by Formula 2, and the buffer layer may include a third compound represented by Formula 3:




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    • wherein, in Formulae 1 to 3,

    • X11 may be C(R11) or N, X12 may be C(R12) or N, X13 may be C(R13) or N, X14 may be C(R14) or N, X15 may be C(R15) or N, X16 may be C(R16) or N, and X17 may be C(R17) or N,

    • X21 to X24, Z21, and Z22 may each independently be O, S, Se, Te, SO, SO2, C(R4)(R5), Si(R4)(R5), or N(R4),

    • L31 to L33 may each independently be a single bond, a C1-C20 alkylene group unsubstituted or substituted with at least one R10a, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,

    • a31 to a33 may each independently be an integer from 1 to 3,

    • if (e.g., when) a31 is 2 or 3, a plurality of L31 may be substantially identical to or different from each other, if (e.g., when) a32 is 2 or 3, a plurality of L32 may be substantially identical to or different from each other, and if (e.g., when) a33 is 2 or 3, a plurality of L33 may be substantially identical to or different from each other,

    • Ar21 and Ar31 to Ar33 may each independently be a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,

    • b21 may be an integer from 1 to 10,

    • R11 to R19, R2, R4, and R5 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkenyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkynyl group unsubstituted or substituted with at least one R10a, a C1-C60 alkoxy group unsubstituted or substituted with at least one R10a, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, a C6-C60 aryloxy group unsubstituted or substituted with at least one R10a, a C6-C60 arylthio group unsubstituted or substituted with at least one R10a, a C7-C60 arylalkyl group unsubstituted or substituted with at least one R10a, a C2-C60 heteroarylalkyl group unsubstituted or substituted with at least one R10a, —C(Q1)(Q2)(Q3), —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), or —P(═O)(Q1)(Q2),

    • at least two selected from among R11 to R19 may optionally be bonded to each other to form a C5-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,

    • R10a may be

    • deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group,

    • a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 aryl alkyl group, a C2-C60 heteroaryl alkyl group, —Si(Q11)(Q12)(Q13), —N(Q11)(Q12), —B(Q11)(Q12), —C(═O)(Q11), —S(═O)2(Q11), —P(═O)(Q11)(Q12), or any combination thereof,

    • a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 aryl alkyl group, or a C2-C60 heteroaryl alkyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 aryl alkyl group, a C2-C60 heteroaryl alkyl group, —Si(Q21)(Q22)(Q23), —N(Q21)(Q22), —B(Q21)(Q22), —C(═O)(Q21), —S(═O)2(Q21), —P(═O)(Q21)(Q22), or any combination thereof, or

    • Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), or —P(═O)(Q31)(Q32), and

    • Q1 to Q3, Q11 to Q13, Q21 to Q23, and Q31 to Q33 may each independently be

    • hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, or

    • a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C7-C60 arylalkyl group, or a C2-C60 heteroarylalkyl group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof.





According to one or more embodiments, an electronic apparatus includes the optoelectronic device.





BRIEF DESCRIPTION OF THE DRAWINGS

The accompanying drawings are included to provide a further understanding of the preceding and other aspects, features, and advantages of certain embodiments of the disclosure are incorporated in and constitute a part of this specification. The drawings illustrate example embodiments and, together with the following description taken in conjunction with the accompanying drawings. In the drawings:



FIG. 1 is a schematic view of an optoelectronic device according to one or more embodiments;



FIG. 2 is a schematic view of a light-emitting device included in an electronic apparatus according to one or more embodiments;



FIG. 3 is a schematic view of an electronic apparatus according to one or more embodiments;



FIG. 4 is a schematic view of an electronic apparatus according to one or more embodiments;



FIG. 5 is a schematic perspective view of electronic equipment including an optoelectronic device according to one or more embodiments;



FIG. 6 is a diagram schematically illustrating the exterior of a vehicle as electronic equipment including an optoelectronic device according to one or more embodiments; and



FIGS. 7A-7C are each a diagram schematically illustrating the interior of the vehicle of FIG. 6.





DETAILED DESCRIPTION

Reference will now be made in more detail to one or more embodiments, examples of which are illustrated in the accompanying drawings, wherein like reference numerals refer to like elements throughout, and duplicative descriptions thereof may not be provided. In this regard, the present embodiments may have different forms and should not be construed as being limited to the descriptions set forth herein. Accordingly, one or more embodiments are merely described in more detail, by referring to the drawings, to explain aspects of the present description. An aspect and a characteristic of the disclosure, and a method of accomplishing these will be apparent if referring to one or more embodiments described with reference to the drawings. The same or corresponding components will be denoted by the same reference numerals, and thus redundant description thereof will not be provided.


As used herein, the term “and/or” includes any and all combinations of one or more of the associated listed items. Expressions such as “at least one of,” “one of,” “selected from,” and “selected from among,” when preceding a list of elements, modify the entire list of elements and do not modify the individual elements of the list. For example, throughout the disclosure, the expression “at least one of a, b or c” indicates only a, only b, only c, both (e.g., simultaneously) a and b, both (e.g., simultaneously) a and c, both (e.g., simultaneously) b and c, all of a, b, and c, or variations thereof.


Unless otherwise defined, all chemical names, technical and scientific terms, and terms defined in common dictionaries should be interpreted as having meanings consistent with the context of the related art, and should not be interpreted in an ideal or overly formal sense. It will be understood that although the terms “first,” “second,” and/or the like may be utilized herein to describe one or more suitable components, these components should not be limited by these terms. These terms are only utilized to distinguish one component from another. Thus, a first element could be termed a second element without departing from the teachings of the present disclosure. Similarly, a second element could be termed a first element. An expression utilized in the singular forms such as “a,” “an,” and “the” are intended to encompass the expression of the plural forms as well, unless it has a clearly different meaning in the context.


It will be further understood that the terms “comprises,” “comprising,” “comprise,” “has,” “have,” “having,” “include,” “includes,” and/or “including,” as utilized herein specify the presence of stated features or elements, but do not preclude the presence or addition of one or more other features or elements.


As used herein, the terms “use,” “using,” and “used” may be considered synonymous with the terms “utilize,” “utilizing,” and “utilized,” respectively.


The term “may” will be understood to refer to “one or more embodiments of the present disclosure,” some of which include the described element and some of which exclude that element and/or include an alternate element. Similarly, alternative language such as “or” refers to “one or more embodiments of the present disclosure,” each including a corresponding listed item.


In the following embodiments, if one or more components such as layers, films, regions, plates, and/or the like are said to be “connected to,” or “on” another component, this may include not only a case in which other components are “immediately on” the layers, films, regions, or plates, but also a case in which other components may be placed therebetween. Sizes of elements in the drawings may be exaggerated for convenience of explanation. In other words, because sizes and thicknesses of components in the drawings are arbitrarily illustrated for convenience of explanation, the following embodiments are not limited thereto.


Spatially relative terms, such as “beneath,” “below,” “lower,” “above,” “upper,” “bottom,” “top,” and the like, may be used herein for ease of description to describe one element or feature's relationship to another element(s) or feature(s) as illustrated in the drawings. It will be understood that the spatially relative terms are intended to encompass different orientations of the device in use or operation in addition to the orientation depicted in the drawings. For example, if the device in the drawings is turned over, elements described as “below” or “beneath” other elements or features would then be oriented “above” or “over” the other elements or features. Thus, the term “below” may encompass both an orientation of above and below. The device may be otherwise oriented (rotated 90 degrees or at other orientations), and the spatially relative descriptors used herein should be interpreted accordingly.


In this context, “consisting essentially of” indicates that any additional components will not materially affect the chemical, physical, optical or electrical properties of the semiconductor film.


Further, in this specification, the phrase “on a plane,” or “plan view,” indicates viewing a target portion from the top, and the phrase “on a cross-section” indicates viewing a cross-section formed by vertically cutting a target portion from the side.


A person of ordinary skill in the art would appreciate, in view of the present disclosure in its entirety, that each suitable feature of the various embodiments of the present disclosure may be combined or combined with each other, partially or entirely, and may be technically interlocked and operated in various suitable ways, and each embodiment may be implemented independently of each other or in conjunction with each other in any suitable manner unless otherwise stated or implied.


Optoelectronic Device

According to an aspect of the disclosure, provided is an optoelectronic device including: a first electrode; a second electrode facing (e.g. opposite to) the first electrode; an optical activation layer arranged between the first electrode and the second electrode; and a buffer layer arranged between the optical activation layer and the second electrode, wherein the optical activation layer may include a first compound represented by Formula 1 and a second compound represented by Formula 2, and the buffer layer may include a third compound represented by Formula 3:




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    • wherein, in Formulae 1 to 3,

    • X11 may be C(R11) or N, X12 may be C(R12) or N, X13 may be C(R13) or N, X14 may be C(R14) or N, X15 may be C(R15) or N, X16 may be C(R16) or N, and X17 may be C(R17) or N,

    • X21 to X24, Z21, and Z22 may each independently be O, S, Se, Te, SO, SO2, C(R4)(R5), Si(R4)(R5), or N(R4),

    • L31 to L33 may each independently be a single bond, a C1-C20 alkylene group unsubstituted or substituted with at least one R10a, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,

    • a31 to a33 may each independently be an integer from 1 to 3,

    • if (e.g., when) a31 is 2 or 3, a plurality of L31 may be substantially identical to or different from each other, if (e.g., when) a32 is 2 or 3, a plurality of L32 may be substantially identical to or different from each other, and if (e.g., when) a33 is 2 or 3, a plurality of L33 may be substantially identical to or different from each other,

    • Ar21 and Ar31 to Ar33 may each independently be a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,

    • b21 may be an integer from 1 to 10,

    • R11 to R19, R2, R4, and R5 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkenyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkynyl group unsubstituted or substituted with at least one R10a, a C1-C60 alkoxy group unsubstituted or substituted with at least one R10a, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, a C6-C60 aryloxy group unsubstituted or substituted with at least one R10a, a C6-C60 arylthio group unsubstituted or substituted with at least one R10a, C7-C60 arylalkyl group unsubstituted or substituted with at least one R10a, a C2-C60 heteroarylalkyl group unsubstituted or substituted with at least one R10a, —C(Q1)(Q2)(Q3), —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), or —P(═O)(Q1)(Q2),

    • at least two selected from among R11 to R19 may optionally be bonded to each other to form a C5-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,

    • R10a may be:

    • deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group;

    • a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 aryl alkyl group, a C2-C60 heteroaryl alkyl group, —Si(Q11)(Q12)(Q13), —N(Q11)(Q12), —B(Q11)(Q12), —C(═O)(Q11), —S(═O)2(Q11), —P(═O)(Q11)(Q12), or any combination thereof;

    • a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 aryl alkyl group, or a C2-C60 heteroaryl alkyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 aryl alkyl group, a C2-C60 heteroaryl alkyl group, —Si(Q21)(Q22)(Q23), —N(Q21)(Q22), —B(Q21)(Q22), —C(═O)(Q21), —S(═O)2(Q21), —P(═O)(Q21)(Q22), or any combination thereof; or

    • —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), or —P(═O)(Q31)(Q32), and

    • Q1 to Q3, Q11 to Q13, Q21 to Q23, and Q31 to Q33 may each independently be

    • hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, or

    • a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C7-C60 arylalkyl group, or a C2-C60 heteroarylalkyl group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof.





In one or more embodiments, the optical activation layer may not include (e.g., may exclude) a fullerene-based compound, a phthalocyanine-based compound, and a subphthalocyanine-based compound.


In one or more embodiments, the optical activation layer may include a first layer adjacent to the first electrode and a second layer adjacent to the buffer layer. The first layer may include the first compound. For example, the first layer may not include (e.g., may exclude) the second compound. The second layer may include the second compound. For example, the second layer may not include (e.g., may exclude) the first compound. For example, the first compound and the second compound may not be mixed.


In one or more embodiments, the optical activation layer may further include a third layer arranged between the first layer and the second layer. The third layer may include the first compound and the second compound. For example, the third layer may be a single layer and may include a mixture of the first compound and the second compound.


In one or more embodiments, the optoelectronic device may further include:

    • a hole transport region arranged between the first electrode and the optical activation layer; and
    • an electron transport region arranged between the buffer layer and the second electrode,
    • wherein the hole transport region may include a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or any combination thereof, and
    • the electron transport region may include a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.


In one or more embodiments, the optical activation layer may be to absorb light having a wavelength of about 400 nanometer (nm) to about 1,000 nm. For example, the first compound may be to absorb light having a wavelength of about 400 nm to about 1,000 nm.


In one or more embodiments, in Formula 1,


X11 may be C(R11), X12 may be C(R12), X13 may be C(R13), X14 may be C(R14), X15 may be C(R15), X16 may be C(R16), and X17 may be C(R17).


In one or more embodiments, R11 to R17 may each independently be:

    • hydrogen, deuterium, —F, —Cl, or a cyano group;
    • a C1-C30 alkyl group or a C1-C30 alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, a cyano group, or any combination thereof; or
    • a C3-C30 aryl group or a C1-C30 heteroaryl group, each unsubstituted or substituted with deuterium, —F, —Cl, a cyano group, —CF3, a C1-C10 alkoxy group, or any combination thereof.


In one or more embodiments, in Formula 1,

    • R18 and R19 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, or a cyano group.


In one or more embodiments, the first compound may be represented by any one of (e.g, selected from among) Formulae 1A to 1E:




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    • wherein, in Formulae 1A to 1E,

    • Y11 and Y12 may each independently be O, S, Se, or Te,

    • R11 to R19 are each as described herein, and

    • R11a to R16a may each independently be as described herein in connection with R10a.





In one or more embodiments, in Formula 2, X21 to X24 may each independently be O or S.


In one or more embodiments, in Formula 2,

    • Ar21 may be a phenyl group unsubstituted or substituted with at least one R10a, a biphenyl group unsubstituted or substituted with at least one R10a, a naphthalene group unsubstituted or substituted with at least one R10a, or a phenylene group unsubstituted or substituted with at least one R10a.


In one or more embodiments, in Formula 2,

    • Z21 and Z22 may each independently be O or N(R4),
    • R4 may be: hydrogen, deuterium, —F, —Cl, or a cyano group;
    • a C1-C30 alkyl group or a C1-C30 alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, a cyano group, or any combination thereof; or
    • a C3-C30 carbocyclic group or a C1-C30 heterocyclic group, each unsubstituted or substituted with deuterium, —F, —Cl, a cyano group, —CF3, a C1-C10 alkoxy group, or any combination thereof.


For example, in Formula 2,

    • Z21 and Z22 may each independently be O or N(R4),
    • R4 may be: hydrogen, deuterium, —F, —Cl, or a cyano group;
    • a C1-C30 alkyl group or a C1-C30 alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, a cyano group, or any combination thereof; or
    • a group represented by any one of Formulae 2-1 to 2-9:




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    • wherein, in Formulae 2-1 to 2-9,

    • c3 may be an integer from 0 to 3,

    • c4 may be an integer from 0 to 4,

    • c5 may be an integer from 0 to 5,

    • c11 may be an integer from 0 to 11,

    • R10a may be deuterium, —F, —Cl, a cyano group, —CF3, or a C1-C10 alkoxy group, and





* indicates a binding site to N.


In one or more embodiments, the second compound may be represented by any one of (e.g, selected from among) Formulae 2A to 2F:




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    • wherein, in Formulae 2A to 2F,

    • X21 to X24, Z21, and Z22 are each as described herein, and

    • R21 to R28 may each independently be as described herein in connection with R2.





In one or more embodiments, in Formula 3,

    • Ar31 to Ar33 may each independently be a benzene group unsubstituted or substituted with at least one R10a, a naphthalene group unsubstituted or substituted with at least one R10a, a fluorene group unsubstituted or substituted with at least one R10a, or a spiro-bifluorene group unsubstituted or substituted with at least one R10a.


In one or more embodiments, in Formula 3,

    • Ar31 to Ar33 may each independently be represented by any one of (e.g, selected from among) Formulae 3-1 to 3-11:




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    • wherein, in Formulae 3-1 to 3-11,

    • d5 may be an integer from 0 to 5,

    • d7 may be an integer from 0 to 7,

    • d8 may be an integer from 0 to 9, and

    • d9 may be an integer from 0 to 9, and

    • indicates a binding site to a neighboring atom.





In one or more embodiments, in Formula 3,

    • L31 to L33 may each independently be a single bond, a phenyl group unsubstituted or substituted with at least one R10a, or a naphthalene group unsubstituted or substituted with at least one R10a.


In one or more embodiments, in Formula 3,

    • L31 to L33 may each independently be a single bond or a group represented by any one of (e.g, selected from among) Formulae 4-1 to 4-49:




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    • wherein, in Formulae 4-1 to 4-49,

    • e3 may be an integer from 0 to 3,

    • e4 may be an integer from 0 to 4,

    • e5 may be an integer from 0 to 5,

    • e6 may be an integer from 0 to 6,

    • e7 may be an integer from 0 to 7, and

    • * and *′ each indicate a binding site to a neighboring atom.





In one or more embodiments, the first compound may be any one of (e.g, selected from among) Compounds P1 to P102:




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In one or more embodiments, the second compound may be any one of (e.g, selected from among) Compounds N1 to N43:




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In one or more embodiments, the third compound may be any one of (e.g, selected from among) Compounds 1 to 148:




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In one or more embodiments, the absolute value of a lowest unoccupied molecular orbital (LUMO) energy level of the third compound may be about 2.0 electron volt (eV) to about 2.5 eV.


In one or more embodiments, the absolute value of a highest occupied molecular orbital (HOMO) energy level of the third compound may be about 5.0 eV to about 7.0 eV.


According to another aspect of the disclosure, provided is an electronic apparatus including the optoelectronic device.


In one or more embodiments, the electronic apparatus may further include: a thin-film transistor electrically connected to the first electrode; an emission layer arranged between the first electrode and the second electrode; and a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or any combination thereof.


In one or more embodiments, the emission layer may not overlap the optical activation layer. For example, the emission layer and the optical activation layer may be arranged apart from each other on a plane.


The optoelectronic device according to the disclosure may include in the optical activation layer the first compound represented by Formula 1 and the second compound represented by Formula 2 and include in the buffer layer the third compound represented by Formula 3. For example, the case of i) not including the first compound and including the second compound and the third compound, ii) not including the second compound and including the first compound and the third compound, or iii) not including the third compound and including the first compound and the second compound may not be applicable to the optoelectronic device.


Accordingly, the charge separation characteristics, charge transport characteristics, and/or the like. may be improved, thereby increasing the external quantum efficiency of the optoelectronic device.


Description of FIGS. 1 and 2


FIG. 1 is a schematic view of an optoelectronic device 30 according to one or more embodiments. The optoelectronic device 30 may include a first electrode 110, a hole transport region 120, an optical activation layer 135, a buffer layer 137, an electron transport region 140, and a second electrode 150.



FIG. 2 is a schematic view of a light-emitting device 10 included in an electronic apparatus according to one or more embodiments. The light-emitting device 10 may include the first electrode 110, the hole transport region 120, an emission layer 130, the electron transport region 140, and the second electrode 150. The light-emitting device 10 may further include a buffer layer arranged between the emission layer 130 and the electron transport region 140.


For example, each of the first electrode 110, the hole transport region 120, the electron transport region 140, and the second electrode 150 of the optoelectronic device 30 may be substantially integrated in one body with each of the first electrode 110, the hole transport region 120, the electron transport region 140, and the second electrode 150 of the light-emitting device 10, respectively. In another example, each of the first electrode 110, the hole transport region 120, the electron transport region 140, and the second electrode 150 of the optoelectronic device 30 may be substantially arranged apart from each of the first electrode 110, the hole transport region 120, the electron transport region 140, and the second electrode 150 of the light-emitting device 10, respectively, but may substantially include the same materials and be formed at the same time.


Hereinafter, the structures of the optoelectronic device 30 and the light-emitting device 10 and a method of manufacturing the same are described with reference to FIGS. 1 and 2.


First Electrode 110

In FIG. 1, a substrate may be additionally located under the first electrode 110 or on the second electrode 150. As the substrate, a glass substrate or a plastic substrate may be used. The substrate may be a flexible substrate. For example, the substrate may include plastics with excellent or suitable heat resistance and durability, such as polyimide, polyethylene terephthalate (PET), polycarbonate, polyethylene naphthalate, polyarylate (PAR), polyetherimide, or any combination thereof.


The first electrode 110 may be formed by depositing or sputtering a material for forming the first electrode 110 on the substrate. When the first electrode 110 is an anode, a high-work function material that facilitates injection of holes may be used as a material for forming the first electrode 110.


The first electrode 110 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. When the first electrode 110 is a transmissive electrode, a material for forming the first electrode 110 may include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or any combination thereof. When the first electrode 110 is a semi-transmissive electrode or a reflective electrode, magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), or any combination thereof may be used as a material for forming the first electrode 110.


The first electrode 110 may have a single-layered structure including a single layer or a multi-layered structure including a plurality of layers. For example, the first electrode 110 may have a three-layer structure of ITO/Ag/ITO.


Hole Transport Region 120

The hole transport region 120 may have i) a single-layer structure including a single layer including a single material, ii) a single-layer structure including a single layer including multiple materials that are different from each other, or iii) a multi-layer structure including multiple layers including multiple different materials that are different from each other.


The hole transport region 120 may include a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or any combination thereof.


For example, the hole transport region 120 may have a multi-layer structure including a hole injection layer/hole transport layer structure, a hole injection layer/hole transport layer/emission auxiliary layer structure, a hole injection layer/emission auxiliary layer structure, a hole transport layer/emission auxiliary layer structure, or a hole injection layer/hole transport layer/electron blocking layer structure, wherein constituent layers of each structure are stacked sequentially from the first electrode 110.


The hole transport region 120 may include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof:




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    • wherein, in Formulae 201 and 202,

    • L201 to L204 may each independently be a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,

    • L205 may be *—O—*′, *—S—*′, *—N(Q201)—*′, a C1-C20 alkylene group unsubstituted or substituted with at least one R10a, a C2-C20 alkenylene group unsubstituted or substituted with at least one R10a, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,

    • xa1 to xa4 may each independently be an integer from 0 to 5,

    • xa5 may be an integer from 1 to 10,

    • R201 to R204 and Q201 may each independently be a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,

    • R201 and R202 may optionally be linked to each other via a single bond, a C1-C5 alkylene group unsubstituted or substituted with at least one R10a, or a C2-C5 alkenylene group unsubstituted or substituted with at least one R10a, to form a C8-C60 polycyclic group (for example, a carbazole group and/or the like) unsubstituted or substituted with at least one R10a (for example, Compound HT16),

    • R203 and R204 may optionally be linked to each other via a single bond, a C1-C5 alkylene group unsubstituted or substituted with at least one R10a, or a C2-C5 alkenylene group unsubstituted or substituted with at least one R10a, to form a C8-C60 polycyclic group unsubstituted or substituted with at least one R10a, and

    • na1 may be an integer from 1 to 4.





For example, each of Formulae 201 and 202 may include at least one of (e.g., selected from among) groups represented by Formulae CY201 to CY217:




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    • wherein, in Formulae CY201 to CY217, R10b and R10c may each be the same as described with respect to R10a, ring CY201 to ring CY204 may each independently be a C3-C20 carbocyclic group or a C1-C20 heterocyclic group, and at least one hydrogen in Formulae CY201 to CY217 may be unsubstituted or substituted with R10a as described herein.





In one or more embodiments, ring CY201 to ring CY204 in Formulae CY201 to CY217 may each independently be a benzene group, a naphthalene group, a phenanthrene group, or an anthracene group.


In one or more embodiments, each of Formulae 201 and 202 may include at least one of (e.g., selected from among) groups represented by Formulae CY201 to CY203.


In one or more embodiments, Formula 201 may include at least one of (e.g., selected from among) the groups represented by Formulae CY201 to CY203 and at least one of (e.g., selected from among) the groups represented by Formulae CY204 to CY217.


In one or more embodiments, in Formula 201, xa1 may be 1, R201 may be a group represented by one of (e.g., selected from among) Formulae CY201 to CY203, xa2 may be 0, and R202 may be a group represented by one of (e.g., selected from among) Formulae CY204 to CY207.


In one or more embodiments, each of Formulae 201 and 202 may not include (e.g., may exclude) a group represented by one of Formulae CY201 to CY203.


In one or more embodiments, each of Formulae 201 and 202 may not include (e.g., may exclude) a group represented by one of Formulae CY201 to CY203, and may include at least one of (e.g., selected from among) the groups represented by Formulae CY204 to CY217.


In one or more embodiments, each of Formulae 201 and 202 may not include (e.g., may exclude) a group represented by one of Formulae CY201 to CY217.


In one or more embodiments, the hole transport region may include at least one of (e.g., selected from among) Compounds HT1 to HT46, m-MTDATA, TDATA, 2-TNATA, NPB(NPD), β-NPB, TPD, Spiro-TPD, Spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphor sulfonic acid (PANI/CSA), polyaniline/poly(4-styrenesulfonate) (PANI/PSS), or any combination thereof:




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A thickness of the hole transport region may be in a range of about 50 Å to about 10,000 Å, for example, about 100 Å to about 4,000 Å. When the hole transport region includes a hole injection layer, a hole transport layer, or any combination thereof, a thickness of the hole injection layer may be in a range of about 100 Å to about 9,000 Å, for example, about 100 Å to about 1,000 Å, and a thickness of the hole transport layer may be in a range of about 50 Å to about 2,000 Å, for example, about 100 Å to about 1,500 Å. When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, satisfactory hole transporting characteristics may be obtained without a substantial increase in driving voltage.


The emission auxiliary layer may serve to increase light-emission efficiency by compensating for an optical resonance distance according to the wavelength of light emitted by the emission layer. The electron blocking layer may serve to prevent or reduce electron leakage from the emission layer to the hole transport region. Materials that may be included in the hole transport region may be included in the emission auxiliary layer and the electron blocking layer.


p-Dopant


The hole transport region may further include, in addition to these materials, a charge-generation material for the improvement of conductive properties. The charge-generation material may be uniformly (e.g., substantially uniformly) or non-uniformly (e.g., substantially non-uniformly) dispersed in the hole transport region (for example, in the form of a single layer including a charge-generation material).


The charge-generation material may be, for example, a p-dopant.


For example, a lowest unoccupied molecular orbital (LUMO) energy level of the p-dopant may be about −3.5 eV or less.


In one or more embodiments, the p-dopant may include a quinone derivative, a cyano group-containing compound, a compound including element EL1 and element EL2, or any combination thereof.


Examples of the quinone derivative are TCNQ, F4-TCNQ, and/or the like.


Examples of the cyano group-containing compound are HAT-CN, and a compound represented by Formula 221:




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    • wherein, in Formula 221,

    • R221 to R223 may each independently be a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, and





at least one of R221 to R223 may each independently be: a C3-C60 carbocyclic group or a C1-C60 heterocyclic group, each substituted with a cyano group; —F; —Cl; —Br; —I; a C1-C20 alkyl group substituted with a cyano group, —F, —Cl, —Br, —I, or any combination thereof; or any combination thereof.


In the compound including element EL1 and element EL2, element EL1 may be metal, metalloid, or any combination thereof, and element EL2 may be non-metal, metalloid, or any combination thereof.


Examples of the metal are an alkali metal (for example, lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), and/or the like); alkaline earth metal (for example, beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), and/or the like); transition metal (for example, titanium (Ti), zirconium (Zr), hafnium (Hf), vanadium (V), niobium (Nb), tantalum (Ta), chromium (Cr), molybdenum (Mo), tungsten (W), manganese (Mn), technetium (Tc), rhenium (Re), iron (Fe), ruthenium (Ru), osmium (Os), cobalt (Co), rhodium (Rh), iridium (Ir), nickel (Ni), palladium (Pd), platinum (Pt), copper (Cu), silver (Ag), gold (Au), and/or the like); post-transition metal (for example, zinc (Zn), indium (In), tin (Sn), and/or the like); and lanthanide metal (for example, lanthanum (La), cerium (Ce), praseodymium (Pr), neodymium (Nd), promethium (Pm), samarium (Sm), europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb), lutetium (Lu), and/or the like).


Examples of the metalloid are silicon (Si), antimony (Sb), and tellurium (Te).


Examples of the non-metal are oxygen (O) and halogen (for example, F, Cl, Br, I, and/or the like).


Examples of the compound including element EL1 and element EL2 are metal oxide, metal halide (for example, metal fluoride, metal chloride, metal bromide, or metal iodide), metalloid halide (for example, metalloid fluoride, metalloid chloride, metalloid bromide, or metalloid iodide), metal telluride, or any combination thereof.


Examples of the metal oxide are tungsten oxide (for example, WO, W2O3, WO2, WO3, W2O5, and/or the like), vanadium oxide (for example, VO, V2O3, VO2, V2O5, and/or the like), molybdenum oxide (for example, MoO, Mo2O3, MoO2, MoO3, Mo2O5, and/or the like), rhenium oxide (for example, ReO3, and/or the like), and/or the like.


Examples of the metal halide are alkali metal halide, alkaline earth metal halide, transition metal halide, post-transition metal halide, and lanthanide metal halide.


Examples of the alkali metal halide are LiF, NaF, KF, RbF, CsF, LiCl, NaCl, KCl, RbCI, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, Lil, Nal, Kl, Rbl, and Csl.


Examples of the alkaline earth metal halide are BeF2, MgF2, CaF2, SrF2, BaF2, BeCl2, MgCl2, CaCl2), SrCl2, BaCl2, BeBr2, MgBr2, CaBr2, SrBr2, BaBr2, Bel2, Mgl2, Cal2, Srl2, and Bal2.


Examples of the transition metal halide are titanium halide (for example, TiF4, TiCl4, TiBr4, Til4, and/or the like), zirconium halide (for example, ZrF4, ZrCl4, ZrBr4, Zrl4, and/or the like), hafnium halide (for example, HfF4, HfCl4, HfBr4, Hfl4, and/or the like), vanadium halide (for example, VF3, VCl3, VBr3, Vl3, and/or the like), niobium halide (for example, NbF3, NbCl3, NbBrs, Nbl3, and/or the like), tantalum halide (for example, TaF3, TaCl3, TaBr3, Tal3, and/or the like), chromium halide (for example, CrF3, CrCl3, CrBr3, Crl3, and/or the like), molybdenum halide (for example, MoF3, MoCl3, MoBr3, Mol3, and/or the like), tungsten halide (for example, WF3, WCl3, WBr3, Wl3, and/or the like), manganese halide (for example, MnF2, MnCl2, MnBr2, Mnl2, and/or the like), technetium halide (for example, TcF2, TcCl2, TcBr2, Tcl2, and/or the like), rhenium halide (for example, ReF2, ReCl2, ReBr2, Rel2, and/or the like), Iron (II) halide (for example, FeF2, FeCl2, FeBr2, Fel2, and/or the like), ruthenium halide (for example, RuF2, RuCl2, RuBr2, Rul2, and/or the like), osmium halide (for example, OsF2, OsCl2, OsBr2, Osl2, and/or the like), cobalt halide (for example, CoF2, COCl2, CoBr2, Col2, and/or the like), rhodium halide (for example, RhF2, RhCl2, RhBr2, Rhl2, and/or the like), iridium halide (for example, IrF2, IrCl2, IrBr2, Irl2, and/or the like), nickel halide (for example, NiF2, NiCl2, NiBr2, Nil2, and/or the like), palladium halide (for example, PdF2, PdCl2, PdBr2, Pdl2, and/or the like), platinum halide (for example, PtF2, PtCl2, PtBr2, Pt12, and/or the like), Copper(I) halide (for example, CuF, CuCl, CuBr, Cul, and/or the like), silver halide (for example, AgF, AgCl, AgBr, Agl, and/or the like), and gold halide (for example, AuF, AuCl, AuBr, Aul, and/or the like).


Examples of the post-transition metal halide are zinc halide (for example, ZnF2, ZnCl2, ZnBr2, Znl2, and/or the like), indium halide (for example, Inl3, and/or the like), tin halide (for example, Snl2, and/or the like), and/or the like.


Examples of the lanthanide metal halide are YbF, YbF2, YbF3, SmF3, YbCl, YbCl2, YbCl3 SmCl3, YbBr, YbBr2, YbBr3, SmBrs, Ybl, Ybl2, Ybl3, Sml3, and/or the like.


Examples of the metalloid halide are antimony halide (for example, SbCl5 and/or the like) and/or the like.


Examples of the metal telluride are alkali metal telluride (for example, Li2Te, Na2Te, K2Te, Rb2Te, Cs2Te, and/or the like), alkaline earth metal telluride (for example, BeTe, MgTe, CaTe, SrTe, BaTe, and/or the like), transition metal telluride (for example, TiTe2, ZrTe2, HfTe2, V2Te3, Nb2Te3, Ta2Te3, Cr2Te3, Mo2Te3, W2Te3, MnTe, TcTe, ReTe, FeTe, RuTe, OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, Cu2Te, CuTe, Ag2Te, AgTe, Au2Te, and/or the like), post-transition metal telluride (for example, ZnTe, and/or the like), and lanthanide metal telluride (for example, LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, and/or the like).


Emission Layer 130

The light-emitting device 10 may include an emission layer 130 on the hole transport region 120.


In one or more embodiments, the emission layer 130 may further include, in addition to one or more suitable organic materials, a metal-containing compound such as an organometallic compound, an inorganic material such as a quantum dot, and/or the like.


The emission layer 130 may include i) two or more emitting units sequentially stacked between the first electrode 110 and the second electrode 150, and ii) a charge generation layer located between the two or more emitting units. When the emission layer 130 includes the emitting units and the charge generation layer as described herein, the light-emitting device 10 may be a tandem light-emitting device.


When the light-emitting device 10 is a full-color light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and/or a blue emission layer, according to a subpixel. In one or more embodiments, the emission layer may have a stacked structure of two or more layers of a red emission layer, a green emission layer, and a blue emission layer, in which the two or more layers contact each other or are separated from each other to emit white light. In one or more embodiments, the emission layer may include two or more materials of a red light-emitting material, a green light-emitting material, and a blue light-emitting material, in which the two or more materials are mixed with each other in a single layer to emit white light.


The emission layer may include a host and a dopant. The dopant may include a phosphorescent dopant, a fluorescent dopant, or any combination thereof.


The amount of the dopant in the emission layer may be from about 0.01 part by weight to about 15 parts by weight based on 100 parts by weight of the host.


In one or more embodiments, the emission layer may include a quantum dot.


In one or more embodiments, the emission layer may include a delayed fluorescence material. The delayed fluorescence material may act as a host or a dopant in the emission layer.


A thickness of the emission layer may be in a range of about 100 Å to about 1,000 Å, for example, about 200 Å to about 600 Å. When the thickness of the emission layer is within these ranges, excellent or suitable light-emission characteristics may be obtained without a substantial increase in driving voltage.


Host

In one or more embodiments, the host may include a compound represented by Formula 301:





[Ar301]xb11—[(L301)xb1—R301]xb21  Formula 301

    • wherein, in Formula 301,
    • Ar301 and L301 may each independently be a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,
    • xb11 may be 1, 2, or 3,
    • xb1 may be an integer from 0 to 5,
    • R301 may be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkenyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkynyl group unsubstituted or substituted with at least one R10a, a C1-C60 alkoxy group unsubstituted or substituted with at least one R10a, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, —Si(Q301)(Q302)(Q303), —N(Q301)(Q302), —B(Q301)(Q302), —C(═O)(Q301), —S(═O)2(Q301), or —P(═O)(Q301)(Q302),
    • xb21 may be an integer from 1 to 5, and
    • Q301 to Q303 are each as described herein with respect to Q1.


For example, if (e.g., when) xb11 in Formula 301 is 2 or more, two or more of Ar301 may be linked to each other via a single bond.


In one or more embodiments, the host may include a compound represented by Formula 301-1, a compound represented by Formula 301-2, or any combination thereof:




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    • wherein, in Formula 301-1 and 301-2,

    • ring A301 to ring A304 may each independently be a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,

    • X301 may be O, S, N[(L304)xb4—R304], C(R304)(R305), or Si(R304)(R305),

    • xb22 and xb23 may each independently be 0, 1, or 2,

    • L301, xb1, and R301 may each be as described herein,

    • L302 to L304 may each independently be as described herein with respect to with L301,

    • xb2 to xb4 may each independently be as described herein with respect to xb1, and

    • R302 to R305 and R311 to R314 may each be as described herein with respect to R301.





In one or more embodiments, the host may include an alkaline earth metal complex, a post-transition metal complex, or any combination thereof. For example, the host may include a Be complex (for example, Compound H55), an Mg complex, a Zn complex, or any combination thereof.


In one or more embodiments, the host may include: at least one of (e.g., selected from among) Compounds H1 to H128; 9,10-di(2-naphthyl)anthracene (ADN); 2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN); 9,10-di-(2-naphthyl)-2-t-butyl-anthracene (TBADN); 4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP); 1,3-di(carbazol-9-yl)benzene (mCP); 1,3,5-tri(carbazol-9-yl)benzene (TCP); or any combination thereof:




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Phosphorescent Dopant

In one or more embodiments, the phosphorescent dopant may include at least one transition metal as a central metal.


The phosphorescent dopant may include a monodentate ligand, a bidentate ligand, a tridentate ligand, a tetradentate ligand, a pentadentate ligand, a hexadentate ligand, or any combination thereof.


The phosphorescent dopant may be electrically neutral.


For example, the phosphorescent dopant may include an organometallic compound represented by Formula 401:




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    • wherein, in Formulae 401 and 402,

    • M may be a transition metal (for example, iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), gold (Au), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh), rhenium (Re), or thulium (Tm)),

    • L401 may be a ligand represented by Formula 402, and xc1 may be 1, 2, or 3, wherein if (e.g., when) xc1 is two or more, two or more of L401 may be substantially identical to or different from each other,

    • L402 may be an organic ligand, and xc2 may be 0, 1, 2, 3, or 4, and if (e.g., when) xc2 is 2 or more, two or more of L402 may be substantially identical to or different from each other,

    • X401 and X402 may each independently be nitrogen or carbon,

    • ring A401 and ring A402 may each independently be a C3-C60 carbocyclic group or a C1-C60 heterocyclic group,

    • T401 may be a single bond, *—O—*′, *—S—*′, *—C(═O)—*′, *—N(Q411)—*′, *—C(Q411)(Q412)—*′, *—C(Q411)═C(Q412)—*′, *—C(Q411)=*′, or *═C═*′,

    • X403 and X404 may each independently be a chemical bond (for example, a covalent bond or a coordination bond), O, S, N(Q413), B(Q413), P(Q413), C(Q413)(Q414), or Si(Q413)(Q414),

    • Q411 to Q414 may each be as described herein with respect to Q1,

    • R401 and R402 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C20 alkyl group unsubstituted or substituted with at least one R10a, a C1-C20 alkoxy group unsubstituted or substituted with at least one R10a, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, —Si(Q401)(Q402)(Q403), —N(Q401)(Q402), —B(Q401)(Q402), —C(═O)(Q401), —S(═O)2(Q401), or —P(═O)(Q401)(Q402),

    • Q401 to Q403 may each be as described herein with respect to Q1,

    • xc11 and xc12 may each independently be an integer from 0 to 10, and

    • * and *′ in Formula 402 each indicate a binding site to M in Formula 401.





For example, in Formula 402, i) X401 may be nitrogen, and X402 may be carbon, or ii) each of X401 and X402 may be nitrogen.


In one or more embodiments, if (e.g., when) xc1 in Formula 401 is 2 or more, two ring A401 in two or more of L401 may be optionally linked to each other via T402, which is a linking group, and two ring A402 may be optionally linked to each other via T403, which is a linking group (see Compounds PD1 to PD4 and PD7). T402 and T403 may each be as described herein with respect to T401.


L402 in Formula 401 may be an organic ligand. For example, L402 may include a halogen group, a diketone group (for example, an acetylacetonate group), a carboxylic acid group (for example, a picolinate group), —C(═O), an isonitrile group, —CN group, a phosphorus group (for example, a phosphine group, a phosphite group, and/or the like), or any combination thereof.


The phosphorescent dopant may include, for example, at least one of (e.g., selected from among) compounds PD1 to PD39, or any combination thereof:




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Fluorescent Dopant

The fluorescent dopant may include an amine group-containing compound, a styryl group-containing compound, or any combination thereof.


For example, the fluorescent dopant may include a compound represented by Formula 501:




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    • wherein, in Formula 501,

    • Ar501, L501 to L503, R501, and R502 may each independently be a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,

    • xd1 to xd3 may each independently be 0, 1, 2, or 3, and

    • xd4 may be 1, 2, 3, 4, 5, or 6.





For example, Ar501 in Formula 501 may be a condensed cyclic group (for example, an anthracene group, a chrysene group, or a pyrene group) in which three or more monocyclic groups are condensed together.


In one or more embodiments, xd4 in Formula 501 may be 2.


In one or more embodiments, the fluorescent dopant may include: at least one of (e.g., selected from among) Compounds FD1 to FD37; DPVBi; DPAVBi; or any combination thereof:




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Delayed Fluorescence Material

The emission layer 130 may include a delayed fluorescence material.


In the specification, the delayed fluorescence material may be selected from among compounds capable of emitting delayed fluorescent light based on a delayed fluorescence emission mechanism.


The delayed fluorescence material included in the emission layer may act as a host or a dopant depending on the type or kind of other materials included in the emission layer.


According to one or more embodiments, the difference between the triplet energy level of the delayed fluorescence material and the singlet energy level of the delayed fluorescence material may be greater than or equal to about 0 eV and less than or equal to about 0.5 eV. When the difference between the triplet energy level (eV) of the delayed fluorescence material and the singlet energy level (eV) of the delayed fluorescence material satisfies the herein-described range, up-conversion from the triplet state to the singlet state of the delayed fluorescence materials may effectively occur, and thus, the luminescence efficiency of the light-emitting device 10 may be improved.


For example, the delayed fluorescence material may include i) a material including at least one electron donor (for example, a π electron-rich C3-C60 cyclic group, such as a carbazole group) and at least one electron acceptor (for example, a sulfoxide group, a cyano group, or a π electron-deficient nitrogen-containing C1-C60 cyclic group), and ii) a material including a C8-C60 polycyclic group in which two or more cyclic groups are condensed while sharing boron (B).


Examples of the delayed fluorescence material may include at least one of (e.g., selected from among) Compounds DF1 to DF14:




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Quantum Dot

The emission layer 130 may include quantum dots.


The term “quantum dot” as used herein refers to a crystal of a semiconductor compound, and may include any material capable of emitting light of one or more suitable emission wavelengths according to the size of the crystal.


A diameter of the quantum dots may be, for example, in a range of about 1 nm to about 10 nm.


The quantum dot may be synthesized by a wet chemical process, a metal organic chemical vapor deposition process, a molecular beam epitaxy process, or any process similar thereto.


The wet chemical process is a method including mixing a precursor material with an organic solvent and then growing a quantum dot particle crystal. When the crystal grows, the organic solvent naturally acts as a dispersant coordinated on the surface of the quantum dot crystal and controls the growth of the crystal so that the growth of quantum dot particles can be controlled or selected through a process which costs lower, and is easier than vapor deposition methods, such as metal organic chemical vapor deposition (MOCVD) or molecular beam epitaxy (MBE),


The quantum dot may include Group II-VI semiconductor compounds, Group III-V semiconductor compounds, Group III-VI semiconductor compounds, Group I-III-VI semiconductor compounds, Group IV-VI semiconductor compounds, a Group IV element or compound, or any combination thereof.


Examples of the Group II-VI semiconductor compound are: a binary compound, such as CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, or MgS; a ternary compound, such as CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, or MgZnS; a quaternary compound, such as CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, or HgZnSTe; or any combination thereof.


Examples of the Group III-V semiconductor compound are: a binary compound, such as GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AISb, InN, InP, InAs, InSb, and/or the like; a ternary compound, such as GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNP, InAlP, InNAs, InNSb, InPAs, InPSb, and/or the like; a quaternary compound, such as GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GalnNSb, GaInPAs, GalnPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb, and/or the like; or any combination thereof. In one or more embodiments, the Group III-V semiconductor compound may further include a Group II element. Examples of the Group III-V semiconductor compound further including a Group II element are InZnP, InGaZnP, InAIZnP, and/or the like.


Examples of the Group III-VI semiconductor compound are: a binary compound, such as GaS, GaSe, Ga2Se3, GaTe, InS, InSe, In2S3, In2Se3, or InTe; a ternary compound, such as InGaS3, or InGaSe3; and any combination thereof.


Examples of the Group I-III-VI semiconductor compound are: a ternary compound such as AgInS, AgInS2, CuInS, CuInS2, CuGaO2, AgGaO2, or AgAlO2; a quaternary compound such as AgInGaS or AgInGaS2; or any combination thereof.


Examples of the Group IV-VI semiconductor compound are: a binary compound, such as SnS, SnSe, SnTe, PbS, PbSe, or PbTe; a ternary compound, such as SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, or SnPbTe; a quaternary compound, such as SnPbSSe, SnPbSeTe, or SnPbSTe; or any combination thereof.


Examples of the Group IV element or compound are: a single element, such as Si, Ge, and/or the like; a binary compound, such as SiC, SiGe, and/or the like; or any combination thereof.


Each element included in a multi-element compound such as the binary compound, the ternary compound, and the quaternary compound may be present at a substantially uniform concentration or non-substantially uniform concentration in a particle.


In one or more embodiments, the quantum dot may have a single structure in which the concentration of each element in the quantum dot is substantially uniform, or a core-shell dual structure. For example, the material included in the core and the material included in the shell may be different from each other.


The shell of the quantum dot may act as a protective layer that prevents chemical degeneration of the core to maintain semiconductor characteristics, and/or as a charging layer that imparts electrophoretic characteristics to the quantum dot. The shell may be a single layer or a multi-layer. The interface between the core and the shell may have a concentration gradient in which the concentration of an element existing in the shell decreases toward the center of the core.


Examples of the shell of the quantum dot may be an oxide of metal, metalloid, or non-metal, a semiconductor compound, and any combination thereof. Examples of the oxide of metal, metalloid, or non-metal are: a binary compound, such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, CO3O4, or NiO; a ternary compound, such as MgAl2O4, CoFe2O4, NiFe2O4, or CoMn2O4; and any combination thereof. Examples of the semiconductor compound are, as described herein, a Group II-VI semiconductor compound; a Group III-V semiconductor compound; a Group III-VI semiconductor compound; a Group I-III-VI semiconductor compound; a Group IV-VI semiconductor compound; and any combination thereof. For example, the semiconductor compound may include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, or any combination thereof.


A full width at half maximum (FWHM) of the emission wavelength spectrum of the quantum dot may be about 45 nm or less, for example, about 40 nm or less, for example, about 30 nm or less, and within these ranges, color purity or color reproducibility may be increased. In some embodiments, because the light emitted through the quantum dot is emitted in all directions, the wide viewing angle may be improved.


In some embodiments, the quantum dot may be in the form of a spherical particle, a pyramidal particle, a multi-arm particle, a cubic nanoparticle, a nanotube particle, a nanowire particle, a nanofiber particle, or a nanoplate particle.


Because the energy band gap may be adjusted by controlling the size of the quantum dot, light having one or more suitable wavelength bands may be obtained from the quantum dot emission layer. Accordingly, by using quantum dots of different sizes, a light-emitting device that emits light of one or more suitable wavelengths may be implemented. In one or more embodiments, the size of the quantum dot may be selected to emit red, green and/or blue light. In some embodiments, the size of the quantum dot may be configured to emit white light by combination of light of one or more suitable colors.


Optical Activation Layer 135

The optoelectronic device 30 may include an optical activation layer 135 on the hole transport region 120. The optical activation layer 135 may be arranged between the hole transport region 120 and the buffer layer 137. For example, the optical activation layer 135 may be arranged between the buffer layer 137 and the hole transfer layer included in the hole transport region 120. In another example, the optical activation layer 135 may be arranged between the buffer layer 137 and the emission auxiliary layer included in the hole transport region 120.


The optical activation layer 135 may include the first compound and the second compound. For example, the first compound and the second compound may be mixed and included in the optical activation layer 135. For example, the optical activation layer 135 may be a single layer including the first compound and the second compound.


The optical activation layer 135 may generate excitons by absorbing light incident onto the electronic apparatus. The excitons may generate holes and electrons. For example, the optical activation layer 135 may be to absorb light to generate an electrical signal. For example, the first compound included in the optical activation layer 135 may serve as a donor providing electrons, and the second compound included in the optical activation layer 135 may serve as an acceptor receiving electrons. Thus, the optoelectronic device 30 including the optical activation layer 135 may serve as an optical sensor. For example, the optoelectronic device 30 may server as a fingerprint recognition sensor, which is to be described in relation to FIG. 3.


Buffer Layer 137

The optoelectronic device 30 may include the buffer layer 137 arranged on the optical activation layer 135. The buffer layer 137 may be arranged between the optical activation layer 135 and the electron transport region 140.


The buffer layer 137 may include the third compound. For example, the buffer layer 137 may not include (e.g., may exclude) the first compound and the second compound.


The buffer layer 137 may control electron injection and prevent or reduce hole leakage.


Electron Transport Region 140

The electron transport region may have: i) a single-layered structure including a single layer including a single material, ii) a single-layered structure including a single layer including a plurality of different materials, or iii) a multi-layered structure including a plurality of layers including different materials.


The electron transport region may include a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.


For example, the electron transport region may have an electron transport layer/electron injection layer structure, a hole blocking layer/electron transport layer/electron injection layer structure, an electron control layer/electron transport layer/electron injection layer structure, or a buffer layer/electron transport layer/electron injection layer structure, the constituting layers of each structure being sequentially stacked from an emission layer.


The electron transport region (for example, the hole blocking layer, the electron control layer, or the electron transport layer in the electron transport region) may include a metal-free compound including at least one π electron-deficient nitrogen-containing C1-C60 cyclic group.


For example, the electron transport region may include a compound represented by Formula 601:





[Ar601]xe11—[(L601)xe1—R601]xe21  Formula 601

    • wherein, in Formula 601,
    • Ar601 and L601 may each independently be a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,
    • xe11 may be 1, 2, or 3,
    • xe1 may be 0, 1, 2, 3, 4, or 5,


R601 may be a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, —Si(Q601)(Q602)(Q603), —C(═O)(Q601), —S(═O)2(Q601), or —P(═O)(Q601)(Q602),

    • Q601 to Q603 may each be as described herein with respect to Q1,


xe21 may be 1, 2, 3, 4, or 5, and


at least one of Ar601, L601, and R601 may each independently be a π electron-deficient nitrogen-containing C1-C60 cyclic group unsubstituted or substituted with at least one R10a.


For example, if (e.g., when) xe11 in Formula 601 is 2 or more, two or more of Ar601 may be linked to each other via a single bond.


In one or more embodiments, Ar601 in Formula 601 may be an anthracene group unsubstituted or substituted with at least one R10a.


In one or more embodiments, the electron transport region may include a compound represented by Formula 601-1:




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    • wherein, in Formula 601-1,

    • X614 may be N or C(R614), X615 may be N or C(R615), X616 may be N or C(R616), and at least one of X614 to X616 may be N,

    • L611 to L613 may each be as described herein with respect to L601,

    • xe611 to xe613 may each be as described herein with respect to xe1,

    • R611 to R613 may each be as described herein with respect to R601, and

    • R614 to R616 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a.





For example, xe1 and xe611 to xe613 in Formulae 601 and 601-1 may each independently be 0, 1, or 2.


The electron transport region may include at least one of (e.g., selected from among) Compounds ET1 to ET45, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq3, BAlq, TAZ, NTAZ, or any combination thereof:




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A thickness of the electron transport region may be from about 100 Å to about 5,000 Å, for example, about 160 Å to about 4,000 Å. When the electron transport region includes a hole blocking layer, an electron control layer, an electron transport layer, or any combination thereof, a thickness of the hole blocking layer, or the electron control layer may each independently be from about 20 Å to about 1,000 Å, for example, about 30 Å to about 300 Å, and a thickness of the electron transport layer may be from about 100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. When the thicknesses of the hole blocking layer, the electron control layer, the electron transport layer, and/or the electron transport region are within these ranges, satisfactory electron transporting characteristics may be obtained without a substantial increase in driving voltage.


The electron transport region (for example, the electron transport layer in the electron transport region) may further include, in addition to the materials described herein, a metal-containing material.


The metal-containing material may include an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The metal ion of an alkali metal complex may be a Li ion, a Na ion, a K ion, a Rb ion, or a Cs ion, and the metal ion of an alkaline earth metal complex may be a Be ion, a Mg ion, a Ca ion, a Sr ion, or a Ba ion. A ligand coordinated with the metal ion of the alkali metal complex or the alkaline earth-metal complex may include a hydroxyquinoline, a hydroxyisoquinoline, a hydroxybenzoquinoline, a hydroxyacridine, a hydroxyphenanthridine, a hydroxyphenyloxazole, a hydroxyphenylthiazole, a hydroxyphenyloxadiazole, a hydroxyphenylthiadiazole, a hydroxyphenylpyridine, a hydroxyphenylbenzimidazole, a hydroxyphenylbenzothiazole, a bipyridine, a phenanthroline, a cyclopentadiene, or any combination thereof.


For example, the metal-containing material may include a Li complex. The Li complex may include, for example, Compound ET-D1 (LiQ) and/or ET-D2:




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The electron transport region may include an electron injection layer that facilitates the injection of electrons from the second electrode 150. The electron injection layer may directly contact the second electrode 150.


The electron injection layer may have: i) a single-layered structure including a single layer including a single material, ii) a single-layered structure including a single layer including a plurality of different materials, or iii) a multi-layered structure including a plurality of layers including different materials.


The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.


The alkali metal may include Li, Na, K, Rb, Cs, or any combination thereof. The alkaline earth metal may include Mg, Ca, Sr, Ba, or any combination thereof. The rare earth metal may include Sc, Y, Ce, Tb, Yb, Gd, or any combination thereof.


The alkali metal-containing compound, the alkaline earth metal-containing compound, and the rare earth metal-containing compound may be oxides, halides (for example, fluorides, chlorides, bromides, or iodides), or tellurides of the alkali metal, the alkaline earth metal, and the rare earth metal, or any combination thereof.


The alkali metal-containing compound may include: alkali metal oxides, such as Li2O, Cs2O, or K2O; alkali metal halides, such as LiF, NaF, CsF, KF, Lil, Nal, Csl, or Kl; or any combination thereof. The alkaline earth metal-containing compound may include an alkaline earth metal compound, such as BaO, SrO, CaO, BaxSr1-xO (wherein x is a real number satisfying the condition of 0<x<1), BaxCa1-xO (wherein x is a real number satisfying the condition of 0<x<1), and/or the like. The rare earth metal-containing compound may include YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3, TbF3, Ybl3, Scl3, Tbl3, or any combination thereof. In one or more embodiments, the rare earth metal-containing compound may include lanthanide metal telluride. Examples of the lanthanide metal telluride are LaTe, CeTe, PrTe, NdTe, PmTe, SmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, La2Te3, Ce2Te3, Pr2Te3, Nd2Te3, Pm2Te3, Sm2Te3, Eu2Te3, Gd2Te3, Tb2Te3, Dy2Te3, Ho2Te3, Er2Te3, Tm2Te3, Yb2Te3, and Lu2Te3.


The alkali metal complex, the alkaline earth-metal complex, and the rare earth metal complex may include i) one of ions of the alkali metal, the alkaline earth metal, and the rare earth metal and ii) a ligand bonded to the metal ion, for example, hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenyl benzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof.


The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof, as described herein. In one or more embodiments, the electron injection layer may further include an organic material (for example, a compound represented by Formula 601).


In one or more embodiments, the electron injection layer may include: i) an alkali metal-containing compound (for example, an alkali metal halide); or ii) a) an alkali metal-containing compound (for example, an alkali metal halide), and b) an alkali metal, an alkaline earth metal, a rare earth metal, or any combination thereof. For example, the electron injection layer may be a KI:Yb co-deposited layer, an Rbl:Yb co-deposited layer, a LiF:Yb co-deposited layer, and/or the like.


When the electron injection layer further includes an organic material, an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth-metal complex, a rare earth metal complex, or any combination thereof may be uniformly (e.g., substantially uniformly) or non-uniformly (e.g., substantially non-uniformly) dispersed in a matrix including the organic material.


A thickness of the electron injection layer may be in a range of about 1 Å to about 100 Å, and, for example, about 3 Å to about 90 Å. When the thickness of the electron injection layer is within the ranges described herein, satisfactory electron injection characteristics may be obtained without a substantial increase in driving voltage.


Second Electrode 150

The second electrode 150 may be arranged on the electron transport region 140. The second electrode 150 may be a cathode, which is an electron injection electrode, and as the material for the second electrode 150, a metal, an alloy, an electrically conductive compound, or any combination thereof, each having a low-work function, may be used.


The second electrode 150 may include Li, Ag, Mg, Al, Al—Li, Ca, Mg—In, Mg—Ag, Yb, Ag—Yb, ITO, IZO, or any combination thereof. The second electrode 150 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.


The second electrode 150 may have a single-layer structure or a multi-layer structure including multiple layers.


Capping Layer

A first capping layer may be located outside (and e.g., on) the first electrode 110, and/or a second capping layer may be located outside (and e.g., on) the second electrode 150. For example, the light-emitting device 10 may have a structure in which the first capping layer, the cathode 110, the emission layer 130, and the anode 150 are sequentially stacked in the stated order, a structure in which the cathode 110, the emission layer 130, the anode 150, and the second capping layer are sequentially stacked in the stated order, or a structure in which the first capping layer, the cathode 110, the emission layer 130, the anode 150, and the second capping layer are sequentially stacked in the stated order.


Light generated in the emission layer 130 of the light-emitting device 10 may pass through the first electrode 110, which is a semi-transmissive electrode or a transmissive electrode, and through the first capping layer to the outside. Light generated in the emission layer 130 of the light-emitting device 10 may pass through the second electrode 150, which is a semi-transmissive electrode or a transmissive electrode, and through the second capping layer to the outside.


The first capping layer and the second capping layer may increase external emission efficiency according to the aspect of constructive interference. Accordingly, the light extraction efficiency of the light-emitting device 10 is increased, so that the luminescence efficiency of the light-emitting device 10 may be improved.


The first capping layer and the second capping layer may each include a material having a refractive index of about 1.6 or more (at 589 nm).


The first capping layer and the second capping layer may each independently be an organic capping layer including an organic material, an inorganic capping layer including an inorganic material, or an organic-inorganic composite capping layer including an organic material and an inorganic material.


At least one of (e.g., selected from among) the first capping layer and/or the second capping layer may each independently include carbocyclic compounds, heterocyclic compounds, amine group-containing compounds, porphine derivatives, phthalocyanine derivatives, naphthalocyanine derivatives, alkali metal complexes, alkaline earth metal complexes, or any combination thereof. Optionally, the carbocyclic compound, the heterocyclic compound, and the amine group-containing compound may be substituted with a substituent including O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof. In one or more embodiments, at least one of (e.g., selected from among) the first capping layer and/or the second capping layer may each independently include an amine group-containing compound.


For example, at least one of (e.g., selected from among) the first capping layer and/or the second capping layer may each independently include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof.


In one or more embodiments, at least one of (e.g., selected from among) the first capping layer and/or the second capping layer may each independently include at least one of (e.g., selected from among) Compounds HT28 to HT33, at least one of (e.g., selected from among) Compounds CP1 to CP6, β-NPB, or any combination thereof:




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Film

The electronic apparatus may further include a film. The film may be, for example, an optical member (or a light control component) (for example, a color filter, a color conversion member, a capping layer, a light extraction efficiency enhancement layer, a selective light absorbing layer, a polarizing layer, a quantum dot-containing layer, or like), a light blocking member (for example, a light reflective layer, a light absorbing layer, and/or the like), a protective member (for example, an insulating layer, a dielectric layer, and/or the like).


Electronic Apparatus

The light-emitting device 10 and the optoelectronic device 30 may be included in one or more suitable electronic apparatuses. For example, the electronic apparatus may be a light-emitting apparatus, an authentication apparatus, and/or the like.


The electronic apparatus (for example, a light-emitting apparatus) may further include, in addition to the light-emitting device 10 and the optoelectronic device 30, i) a color filter, ii) a color-conversion layer, or iii) a color filter and a color-conversion layer. The color filter and/or the color conversion layer may be located in at least one direction in which light emitted from the light-emitting device travels. For example, the light emitted from the light-emitting device may be blue light or white light. For details on the light-emitting device, related description provided herein may be referred to. In one or more embodiments, the color conversion layer may include a quantum dot. The quantum dot may be, for example, a quantum dot as described herein.


The electronic apparatus may include a first substrate. The first substrate may include a plurality of subpixel areas, the color filter may include a plurality of color filter areas respectively corresponding to the subpixel areas, and the color conversion layer may include a plurality of color conversion areas respectively corresponding to the subpixel areas.


A pixel defining film may be located among the subpixel areas to define each of the subpixel areas.


The color filter may further include a plurality of color filter areas and light-shielding patterns located among the color filter areas, and the color conversion layer may further include a plurality of color conversion areas and light-shielding patterns located among the color conversion areas.


The plurality of color filter areas (or the plurality of color conversion areas) may include a first area emitting first color light, a second area emitting second color light, and/or a third area emitting third color light, wherein the first color light, the second color light, and/or the third color light may have different maximum emission wavelengths from one another. For example, the first color light may be red light, the second color light may be green light, and the third color light may be blue light. For example, the plurality of color filter areas (or the plurality of color conversion areas) may include quantum dots. In particular, the first area may include a red quantum dot, the second area may include a green quantum dot, and the third area may not include (e.g., may exclude) a (e.g., any) quantum dot. For details on the quantum dot, related descriptions provided herein may be referred to. The first area, the second area, and/or the third area may each include a scatter.


For example, the light-emitting device may be to emit first light, the first area may be to absorb the first light to emit first-first color light, the second area may be to absorb the first light to emit second-first color light, and the third area may be to absorb the first light to emit third-first color light. In this regard, the first-first color light, the second-first color light, and the third-first color light may have different maximum emission wavelengths. In particular, the first light may be blue light, the first-first color light may be red light, the second-first color light may be green light, and the third-first color light may be blue light.


The electronic apparatus may further include a thin-film transistor, in addition to the optoelectronic device and the light-emitting device. The thin-film transistor may include a source electrode, a drain electrode, and an activation layer, wherein any one of the source electrode and the drain electrode may be electrically connected to any one of the first electrode and the second electrode of the light-emitting device.


The thin-film transistor may further include a gate electrode, a gate insulating film, and/or the like.


The activation layer may include crystalline silicon, amorphous silicon, an organic semiconductor, an oxide semiconductor, and/or the like.


The electronic apparatus may further include a sealing portion for sealing the light-emitting device. The sealing portion may be located between the color filter and/or the color conversion layer and the light-emitting device. The sealing portion allows light from the light-emitting device to be extracted to the outside, and concurrently (e.g., simultaneously) prevents ambient air and moisture from penetrating into the light-emitting device. The sealing portion may be a sealing substrate including a transparent glass substrate or a plastic substrate. The sealing portion may be a thin-film encapsulation layer including at least one layer of an organic layer and/or an inorganic layer. When the sealing portion is a thin film encapsulation layer, the electronic apparatus may be flexible.


Various functional layers may be additionally located on the sealing portion, in addition to the color filter and/or the color conversion layer, according to the use of the electronic apparatus. Examples of the functional layers may include a touch screen layer, a polarizing layer, and/or the like. The touch screen layer may be a pressure-sensitive touch screen layer, a capacitive touch screen layer, or an infrared touch screen layer. The authentication apparatus may be, for example, a biometric authentication apparatus that authenticates an individual by using biometric information of a living body (for example, fingertips, pupils, and/or the like).


The authentication apparatus may further include, in addition to the optoelectronic device and the light-emitting device, a biometric information collector.


The electronic apparatus may be applied to one or more suitable displays, light sources, lighting, personal computers (for example, a mobile personal computer), mobile phones, digital cameras, electronic organizers, electronic dictionaries, electronic game machines, medical instruments (for example, electronic thermometers, sphygmomanometers, blood glucose meters, pulse measurement devices, pulse wave measurement devices, electrocardiogram displays, ultrasonic diagnostic devices, or endoscope displays), fish finders, one or more suitable measuring instruments, meters (for example, meters for a vehicle, an aircraft, and a vessel), projectors, and/or the like.


Electronic Equipment

The optoelectronic device may be included in one or more suitable types (kinds) of electronic equipment.


For example, the electronic equipment including the optoelectronic device may be any one selected from among a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, a light for indoor or outdoor lighting and/or signaling, a head-up display, a fully or partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a telephone, a mobile phone, a tablet, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a micro display, a 3D display, a virtual or augmented-reality display, a vehicle, a video wall including multiple displays tiled together, a theater or stadium screen, a phototherapy device, and a signboard.


Because the optoelectronic device has excellent or suitable photoelectric properties and/or the like, the electronic equipment including the optoelectronic device may have an optical sensor function such as a fingerprint recognition sensor and/or the like.


Description of FIGS. 3 and 4


FIG. 3 is a cross-sectional view of an electronic apparatus according to one or more embodiments.


The electronic apparatus of FIG. 3 may include a substrate 100, a thin-film transistor (TFT), the light-emitting device 10, the optoelectronic device 30, and an encapsulation portion 300. The optoelectronic device 30 of FIG. 3 may be the optoelectronic device 30 described in relation to FIG. 1; however, the disclosure is not limited thereto.


The substrate 100 may be a flexible substrate, a glass substrate, or a metal substrate. A barrier layer 210 may be arranged on the substrate 100. The barrier layer 210 may prevent or reduce penetration of impurities through the substrate 100 and provide a flat surface on the substrate 100.


The TFT may be arranged on the barrier layer 210. The TFT may include an activation layer 220, a gate electrode 240, a source electrode 260, and a drain electrode 270.


The activation layer 220 may include an inorganic semiconductor such as silicon or polysilicon, an organic semiconductor, or an oxide semiconductor, and may include a source region, a drain region, and a channel region.


A gate insulating film 230 for insulating the activation layer 220 from the gate electrode 240 may be located on the activation layer 220, and the gate electrode 240 may be located on the gate insulating film 230.


An interlayer insulating film 250 may be located on the gate electrode 240. The interlayer insulating film 250 may be located between the gate electrode 240 and the source electrode 260 and between the gate electrode 240 and the drain electrode 270, to insulate from one another.


The source electrode 260 and the drain electrode 270 may be located on the interlayer insulating film 250. The interlayer insulating film 250 and the gate insulating film 230 may be formed to expose the source region and the drain region of the active layer 220, and the source electrode 260 and the drain electrode 270 may be arranged in contact with the exposed portions of the source region and the drain region of the active layer 220.


The TFT electrically connected to the light-emitting device 10 may be to transmit an electrical signal for driving the light-emitting device 10. The TFT electrically connected to the optoelectronic device 30 may be to transmit an electrical signal generated by the optoelectronic device 30. The TFT may be covered and protected by a passivation layer 280. The passivation layer 280 may include an inorganic insulating film, an organic insulating film, or any combination thereof. The light-emitting device 10 and the optoelectronic device 30 may be arranged on the passivation layer 280.


The light-emitting device may include the first electrode 110, the hole transport region 120, the emission layer 130, the electron transport region 140, and the second electrode 150. The light-emitting device may further include the buffer layer 137 arranged between the emission layer 130 and the electron transport region 140. The optoelectronic device 30 may include the first electrode 110, the hole transport region 120, the optical activation layer 135, the buffer layer 137, the electron transport region 140, and the second electrode 150.


The first electrode 110 may be located on the passivation layer 280. The passivation layer 280 may expose a certain portion of the source electrode 260 and the drain electrode 270 without completely covering the source electrode 260 and the drain electrode 270, and the first electrode 110 may be arranged to be connected to the exposed portion of the source electrode 260 and the drain electrode 270.


A pixel defining layer 290 including an insulating material may be located on the first electrode 110. The pixel defining layer 290 may expose a certain region of the first electrode 110. The pixel defining layer 290 may be a polyimide or polyacrylic organic film.


The hole transport region 120 may be arranged on the pixel defining layer 290. The hole transport region 120 included in the light-emitting device 10 and the hole transport region 120 included in the optoelectronic device 30 may be integrated. The hole transport region 120 included in the light-emitting device 10 and the hole transport region 120 included in the optoelectronic device 30 may be arranged on the pixel defining layer 290, may be connected to each other, may include substantially the same material, and may be formed at substantially the same time.


Each of the emission layer 130 and the optical activation layer 135 may be arranged on the hole transport region 120. Each of the emission layer 130 and the optical activation layer 135 may overlap the certain region of the first electrode 110, which is exposed by the pixel defining layer 290.


The buffer layer 137 may be arranged on the optical activation layer 135. When the light-emitting device 10 includes the buffer layer 137, the buffer layer 137 included in the optoelectronic device 30 may extend and be arranged on the emission layer 130. In this case, the buffer layer 137 included in the light-emitting device 10 and the buffer layer 137 included in the optoelectronic device 30 may be integrated. The buffer layer 137 included in the light-emitting device 10 and the buffer layer 137 included in the optoelectronic device 30 may be arranged on the pixel defining layer 290, may be connected to each other, may include substantially the same material, and may be formed at substantially the same time.


The electron transport region 140 may be arranged on the emission layer 130 and the optical activation layer 135. The electron transport region 140 included in the light-emitting device 10 and the electron transport region 140 included in the optoelectronic device 30 may be integrated. The electron transport region 140 included in the light-emitting device 10 and the electron transport region 140 included in the optoelectronic device 30 may be arranged on the pixel defining layer 290, may be connected to each other, may include substantially the same material, and may be formed at substantially the same time.


The second electrode 150 may be arranged on the electron transport region 140. The second electrode 150 included in the light-emitting device 10 and the second electrode 150 included in the optoelectronic device 30 may be integrated. The second electrode 150 included in the light-emitting device 10 and the second electrode 150 included in the optoelectronic device 30 may be arranged on the pixel defining layer 290, may be connected to each other, may include substantially the same material, and may be formed at substantially the same time.


A capping layer 170 may be further formed on the second electrode 150. The capping layer 170 may be formed to cover the second electrode 150.


The encapsulation portion 300 may be located on the capping layer 170. The encapsulation portion 300 may be arranged on the light-emitting device 10 and the optoelectronic device 30 to protect the light-emitting device 10 and the optoelectronic device 30 from moisture or oxygen. The encapsulation portion 300 may include: an inorganic film including silicon nitride (SiNx), silicon oxide (SiOx), indium tin oxide, indium zinc oxide, or any combination thereof; an organic film including polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, an acrylic resin (for example, polymethyl methacrylate, polyacrylic acid, and/or the like), an epoxy-based resin (for example, aliphatic glycidyl ether (AGE), and/or the like), or any combination thereof; or any combination of the inorganic films and the organic films.


The light-emitting device 10 may be to emit light (L1, L2, and L3). For example, the light (L1, L2, and L3) may be green light.


Light L3 of the emitted light (L1, L2, and L3) may be incident onto an object 600 outside the electronic apparatus. For example, the object 600 may be a finger of a user of the electronic apparatus. Light L3′ reflected from the object 600 may be incident onto the optoelectronic device 30.


The optical activation layer 135 may generate excitons by absorbing incident light L3′. The excitons may generate holes and electrons. For example, the optical activation layer 135 may be to absorb light to generate electrical signal. For example, the organic compound included in the optical activation layer 135 may serve as a donor providing electrons, and the electron withdrawing compound included in the optical activation layer 135 may serve as an acceptor receiving electrons. For example, the optoelectronic device 30 may detect energy of the light L3′ and convert the same into an electrical signal. Accordingly, the optoelectronic device 30 may recognize the aspect 600 which has contacted or approached the electronic apparatus. Thus, the optoelectronic device 30 including the optical activation layer 135 may serve as an optical sensor (for example, a fingerprint recognition sensor).



FIG. 4 is a cross-sectional view of an electronic apparatus according to one or more embodiments.


The electronic apparatus of FIG. 4 is the same as the electronic apparatus of FIG. 3, except that a light-shielding pattern 500 and a functional region 400 are additionally arranged on the encapsulation portion 300. The functional region 400 may be i) a color filter area, ii) a color conversion area, or iii) a combination of the color filter area and the color conversion area. In one or more embodiments, the light-emitting device included in the electronic apparatus of FIG. 4 may be a tandem light-emitting device.


Description of FIG. 5


FIG. 5 is a schematic perspective view of electronic equipment 1 including the optoelectronic device according to one or more embodiments. The electronic equipment 1 may be, as an apparatus that displays a moving image or still image, a portable electronic equipment, such as a mobile phone, a smart phone, a tablet personal computer (PC), a mobile communication terminal, an electronic notebook, an electronic book, a portable multimedia player (PMP), a navigation, or a ultra mobile PC (UMPC) as well as one or more suitable products, such as a television, a laptop, a monitor, a billboards, or an Internet of things (IOT). The electronic equipment 1 may be such a product as described herein or a part thereof. In some embodiments, the electronic equipment 1 may be a wearable device such as a smart watch, a watch phone, a glasses-type or kind display, a head mounted display (HMD), or a part thereof. However, embodiments of the disclosure are not limited thereto. For example, the electronic equipment 1 may be a dashboard of a vehicle, a center information display (CID) provided at a center fascia or a dashboard of a vehicle, a room mirror display functioning as a side mirror of a vehicle, a display provided at a backseat entertainment system or at the back of the front seat of a vehicle, a head up display (HUD) arranged at the front of a vehicle or projected on a front window of a vehicle, or a computer generated hologram augmented reality HUD (CGH AR HUD). FIG. 5 illustrates a case in which the electronic equipment 1 is a smartphone for convenience of explanation.


The electronic equipment 1 may include a display area DA and a non-display area NDA outside the display area DA. The electronic equipment may implement an image through an array of a plurality of pixels that are two-dimensionally arranged in the display area DA.


The non-display area NDA is an area that does not display an image, and may entirely be around (e.g., surround) the display area DA. In the non-display area NDA, a driver for providing an electrical signal or power to the light-emitting arranged in the display area DA may be arranged. On the non-display area NDA, a pad, which is an area to which an electronic element or a printing circuit board may be electrically connected, may be arranged.


In the electronic equipment 1, a length in the x-axis direction and a length in the y-axis direction may be different from each other. In one or more embodiments, as shown in FIG. 5, the length in the x-axis direction may be less than the length in the y-axis direction. In one or more embodiments, the length in the x-axis direction may be the same as the length in the y-axis direction. In one or more embodiments, the length in the x-axis direction may be longer than the length in the y-axis direction.


Descriptions of FIGS. 6 and 7A to 7C


FIG. 6 is a diagram illustrating the exterior of a vehicle 1000 as electronic equipment including an optoelectronic device according to one or more embodiments. FIGS. 7A to 7C are each a diagram schematically illustrating the interior of the vehicle 1000 of FIG. 6.


Referring to FIGS. 6 and 7A to 7C, the vehicle 1000 may refer to one or more suitable apparatuses for moving a subject to be transported, such as a human, an object, or an animal, from a departure point to a destination point. The vehicle 1000 may include a vehicle traveling on a road or track, a vessel moving over a sea or river, an airplane flying in the sky using the action of air, and/or the like.


The vehicle 1000 may travel on a road or a track. The vehicle 1000 may move in a set or predetermined direction according to the rotation of at least one wheel. For example, the vehicle 1000 may include a three-wheeled or four-wheeled vehicle, a construction machine, a two-wheeled vehicle, a prime mover device, a bicycle, and a train running on a track.


The vehicle 1000 may include a body having an interior and an exterior, and a chassis in which mechanical apparatuses necessary for driving are installed as other parts except for the body. The exterior of the vehicle body may include a front panel, a bonnet, a roof panel, a rear panel, a trunk, a pillar provided at a boundary between doors, and/or the like. The chassis of the vehicle 1000 may include a power generating device, a power transmitting device, a driving device, a steering device, a braking device, a suspension device, a transmission device, a fuel device, front and rear wheels, left and right wheels, and/or the like.


The vehicle 1000 may include a side window glass 1100, a front window glass 1200, a side mirror 1300, a cluster 1400, a center fascia 1500, a passenger seat dashboard 1600, and a display apparatus 2.


The side window glass 1100 and the front window glass 1200 may be partitioned by a pillar arranged between the side window glass 1100 and the front window glass 1200.


The side window glass 1100 may be installed on the side of the vehicle 1000. In one or more embodiments, the side window glass 1100 may be installed on a door of the vehicle 1000. A plurality of side window glasses 1100 may be provided and may face each other. In one or more embodiments, the side window glass 1100 may include a first side window glass 1110 and a second side window glass 1120. In one or more embodiments, the first side window glass 1110 may be arranged adjacent to the cluster 1400. The second side window glass 1120 may be arranged adjacent to the passenger seat dashboard 1600.


In one or more embodiments, the side window glasses 1100 may be spaced and/or apart (e.g., spaced apart or separated) from each other in the x-direction or the −x-direction. For example, the first side window glass 1110 and the second side window glass 1120 may be spaced and/or apart (e.g., spaced apart or separated) from each other in the x direction or the −x direction. For example, an imaginary straight line L connecting the side window glasses 1100 may extend in the x-direction or the −x-direction. For example, an imaginary straight line L connecting the first side window glass 1110 and the second side window glass 1120 to each other may extend in the x direction or the −x direction.


The front window glass 1200 may be installed in the front of the vehicle 1000. The front window glass 1200 may be arranged between the side window glasses 1100 facing (e.g. opposite to) each other.


The side mirror 1300 may provide a rear view of the vehicle 1000. The side mirror 1300 may be installed on the exterior of the vehicle body. In one or more embodiments, a plurality of side mirrors 1300 may be provided. Any one of the plurality of side mirrors 1300 may be arranged outside the first side window glass 1110. The other one of the plurality of side mirrors 1300 may be arranged outside the second side window glass 1120.


The cluster 1400 may be arranged in front of the steering wheel. The cluster 1400 may include a tachometer, a speedometer, a coolant thermometer, a fuel gauge turn indicator, a high beam indicator, a warning lamp, a seat belt warning lamp, an odometer, a tachograph, an automatic shift selector indicator lamp, a door open warning lamp, an engine oil warning lamp, and/or a low fuel warning light.


The center fascia 1500 may include a control panel on which a plurality of buttons for adjusting an audio device, an air conditioning device, and a heater of a seat are arranged. The center fascia 1500 may be arranged on one side of the cluster 1400.


A passenger seat dashboard 1600 may be spaced and/or apart (e.g., spaced apart or separated) from the cluster 1400 with the center fascia 1500 arranged therebetween. In one or more embodiments, the cluster 1400 may be arranged to correspond to a driver seat, and the passenger seat dashboard 1600 may be arranged to correspond to a passenger seat. In one or more embodiments, the cluster 1400 may be adjacent to the first side window glass 1110, and the passenger seat dashboard 1600 may be adjacent to the second side window glass 1120.


In one or more embodiments, the display apparatus 2 may include a display panel 3, and the display panel 3 may display an image. The display apparatus 2 may be arranged inside the vehicle 1000. In one or more embodiments, the display apparatus 2 may be arranged between the side window glasses 1100 facing (e.g. opposite to) each other. The display apparatus 2 may be arranged on at least one of the cluster 1400, the center fascia 1500, and the passenger seat dashboard 1600.


The display apparatus 2 may include an organic light-emitting display apparatus, an inorganic electroluminescent (EL) display apparatus, a quantum dot display apparatus, and/or the like. Hereinafter, an organic light-emitting display apparatus including the optoelectronic device and the light-emitting device according to one or more embodiments of the disclosure will be described as an example, but one or more suitable types (kinds) of display apparatuses as described herein may be used in embodiments of the disclosure.


Referring to FIG. 7A, the display apparatus 2 may be arranged on the center fascia 1500. In one or more embodiments, the display apparatus 2 may display navigation information. In one or more embodiments, the display apparatus 2 may display audio, video, or information regarding vehicle settings.


Referring to FIG. 7B, the display apparatus 2 may be arranged on the cluster 1400. When the display apparatus 2 is arranged on the cluster 1400, the cluster 1400 may display driving information and/or the like through the display apparatus 2. For example, the cluster 1400 may be implemented digitally. The digital cluster 1400 may display vehicle information and driving information as images. For example, a needle and a gauge of a tachometer and one or more suitable warning light icons may be displayed by a digital signal.


Referring to FIG. 7C, the display apparatus 2 may be arranged on the passenger seat dashboard 1600. The display apparatus 2 may be embedded in the passenger seat dashboard 1600 or arranged on the passenger seat dashboard 1600. In one or more embodiments, the display apparatus 2 arranged on the passenger seat dashboard 1600 may display an image related to information displayed on the cluster 1400 and/or information displayed on the center fascia 1500. In one or more embodiments, the display apparatus 2 arranged on the passenger seat dashboard 1600 may display information different from information displayed on the cluster 1400 and/or information displayed on the center fascia 1500.


Manufacturing Method

The layers constituting the hole transport region, the emission layer, the optical activation layer, and the layers constituting the electron transport region may be formed in a specific region by using one or more suitable methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, ink-jet printing, laser printing, and laser-induced thermal imaging.


When the layers constituting the hole transport region, the emission layer, the optical activation layer, and the layers constituting the electron transport region may each independently be formed by vacuum-deposition, the vacuum-deposition may be performed at a deposition temperature in a range of about 100° C. to about 500° C., at a vacuum degree in a range of about 10−8 torr to about 10−3 torr, and at a deposition rate in a range of about 0.01 Å/sec to about 100 Å/sec, depending on the material to be included in each layer and the structure of each layer to be formed.


DEFINITION OF TERMS

The term “C3-C60 carbocyclic group” as used herein refers to a cyclic group including carbon only as a ring-forming atom and having 3 to 60 carbon atoms. The term “C1-C60 heterocyclic group” as used herein refers to a cyclic group that has 1 to 60 carbon atoms and further has, in addition to carbon, a heteroatom as a ring-forming atom. The C3-C60 carbocyclic group and the C1-C60 heterocyclic group may each be a monocyclic group including one ring or a polycyclic group in which two or more rings are condensed with each other. For example, the C1-C60 heterocyclic group has 3 to 61 ring-forming atoms.


The “cyclic group” as used herein may include both (e.g., simultaneously) the C3-C60 carbocyclic group and the C1-C60 heterocyclic group.


The term “π electron-rich C3-C60 cyclic group” as used herein refers to a cyclic group that has 3 to 60 carbon atoms and does not include *—N═*′ as a ring-forming moiety.


The term “π electron-deficient nitrogen-containing C1-C60 cyclic group” as used herein refers to a heterocyclic group that has 1 to 60 carbon atoms and includes *—N=*′ as a ring-forming moiety.


For example, the C3-C60 carbocyclic group may be i) Group T1 or ii) a condensed cyclic group in which two or more Groups T1 are condensed with each other (for example, a cyclopentadiene group, an adamantane group, a norbornane group, a benzene group, a pentalene group, a naphthalene group, an azulene group, an indacene group, an acenaphthylene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a perylene group, a pentaphene group, a heptalene group, a naphthacene group, a picene group, a hexacene group, a pentacene group, a rubicene group, a coronene group, an ovalene group, an indene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, an indenophenanthrene group, or an indenoanthracene group),

    • the C1-C60 heterocyclic group may be i) Group T2, ii) a condensed cyclic group in which two or more Groups T2 are condensed with each other, or iii) a condensed cyclic group in which at least one Group T2 and at least one Group T1 are condensed with each other (for example, a pyrrole group, a thiophene group, a furan group, an indole group, a benzoindole group, a naphthoindole group, an isoindole group, a benzoisoindole group, a naphthoisoindole group, a benzosilole group, a benzothiophene group, a benzofuran group, a carbazole group, a dibenzosilole group, a dibenzothiophene group, a dibenzofuran group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, a benzosilolocarbazole group, a benzoindolocarbazole group, a benzocarbazole group, a benzonaphthofuran group, a benzonaphthothiophene group, a benzonaphthosilole group, a benzofurodibenzofuran group, a benzofurodibenzothiophene group, a benzothienodibenzothiophene group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzoisoxazole group, a benzothiazole group, a benzoisothiazole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a quinoxaline group, a benzoquinoxaline group, a quinazoline group, a benzoquinazoline group, a phenanthroline group, a cinnoline group, a phthalazine group, a naphthyridine group, an imidazopyridine group, an imidazopyrimidine group, an imidazotriazine group, an imidazopyrazine group, an imidazopyridazine group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzothiophene group, an azadibenzofuran group, and/or the like.),
    • the π electron-rich C3-C60 cyclic group may be i) Group T1, ii) a condensed cyclic group in which two or more Groups T1 are condensed with each other, iii) Group T3, iv) a condensed cyclic group in which two or more Groups T3 are condensed with each other, or v) a condensed cyclic group in which at least one Group T3 and at least one Group T1 are condensed with each other (for example, the C3-C60 carbocyclic group, a 1H-pyrrole group, a silole group, a borole group, a 2H-pyrrole group, a 3H-pyrrole group, a thiophene group, a furan group, an indole group, a benzoindole group, a naphthoindole group, an isoindole group, a benzoisoindole group, a naphthoisoindole group, a benzosilole group, a benzothiophene group, a benzofuran group, a carbazole group, a dibenzosilole group, a dibenzothiophene group, a dibenzofuran group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, a benzosilolocarbazole group, a benzoindolocarbazole group, a benzocarbazole group, a benzonaphthofuran group, a benzonaphthothiophene group, a benzonaphthosilole group, a benzofurodibenzofuran group, a benzofurodibenzothiophene group, a benzothienodibenzothiophene group, and/or the like.), and
    • the π electron-deficient nitrogen-containing C1-C60 cyclic group may be i) Group T4, ii) a condensed cyclic group in which two or more Groups T4 are condensed with each other, iii) a condensed cyclic group in which at least one Group T4 and at least one Group T1 are condensed with each other, iv) a condensed cyclic group in which at least one Group T4 and at least one Group T3 are condensed with each other, or v) a condensed cyclic group in which at least one Group T4, at least one Group T1, and at least one Group T3 are condensed with one another (for example, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzoisoxazole group, a benzothiazole group, a benzoisothiazole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a quinoxaline group, a benzoquinoxaline group, a quinazoline group, a benzoquinazoline group, a phenanthroline group, a cinnoline group, a phthalazine group, a naphthyridine group, an imidazopyridine group, an imidazopyrimidine group, an imidazotriazine group, an imidazopyrazine group, an imidazopyridazine group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzothiophene group, an azadibenzofuran group, and/or the like).


Group T1 may be a cyclopropane group, a cyclobutane group, a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclooctane group, a cyclobutene group, a cyclopentene group, a cyclopentadiene group, a cyclohexene group, a cyclohexadiene group, a cycloheptene group, an adamantane group, a norbornane (or bicyclo[2.2.1]heptane) group, a norbornene group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.2]octane group, or a benzene group.


Group T2 may be a furan group, a thiophene group, a 1H-pyrrole group, a silole group, a borole group, a 2H-pyrrole group, a 3H-pyrrole group, an imidazole group, a pyrazole group, a triazole group, a tetrazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, an azasilole group, an azaborole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a tetrazine group, a pyrrolidine group, an imidazolidine group, a dihydropyrrole group, a piperidine group, a tetrahydropyridine group, a dihydropyridine group, a hexahydropyrimidine group, a tetrahydropyrimidine group, a dihydropyrimidine group, a piperazine group, a tetrahydropyrazine group, a dihydropyrazine group, a tetrahydropyridazine group, or a dihydropyridazine group.


Group T3 may be a furan group, a thiophene group, a 1H-pyrrole group, a silole group, or a borole group.


Group T4 may be a 2H-pyrrole group, a 3H-pyrrole group, an imidazole group, a pyrazole group, a triazole group, a tetrazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, an azasilole group, an azaborole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, or a tetrazine group.


The terms “the cyclic group, the C3-C60 carbocyclic group, the C1-C60 heterocyclic group, the π electron-rich C3-C60 cyclic group, or the rr electron-deficient nitrogen-containing C1-C60 cyclic group” as used herein refer to a group condensed to any cyclic group, a monovalent group, or a polyvalent group (for example, a divalent group, a trivalent group, a tetravalent group, and/or the like.) according to the structure of a formula for which the corresponding term is used.


For example, the “benzene group” may be a benzo group, a phenyl group, a phenylene group, and/or the like, which may be easily understood by one of ordinary skill in the art according to the structure of a formula including the “benzene group.”


Examples of the monovalent C3-C60 carbocyclic group and monovalent C1-C60 heterocyclic group are a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group.


Examples of the divalent C3-C60 carbocyclic group and the divalent C1-C60 heterocyclic group are a C3-C10 cycloalkylene group, a C1-C10 heterocycloalkylene group, a C3-C10 cycloalkenylene group, a C1-C10 heterocycloalkenylene group, a C6-C60 arylene group, a C1-C60 heteroarylene group, a divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group.


The term “C1-C60 alkyl group” as used herein refers to a linear or branched aliphatic hydrocarbon monovalent group that has one to sixty carbon atoms, and specific examples thereof are a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, and a tert-decyl group.


The term “C1-C60 alkylene group” as used herein refers to a divalent group having the same structure as the C1-C60 alkyl group.


The term “C2-C60 alkenyl group” as used herein refers to a monovalent hydrocarbon group having at least one carbon-carbon double bond in the middle or at the terminus of the C2-C60 alkyl group, and examples thereof are an ethenyl group, a propenyl group, and a butenyl group.


The term “C2-C60 alkenylene group” as used herein refers to a divalent group having the same structure as the C2-C60 alkenyl group.


The term “C2-C60 alkynyl group” as used herein refers to a monovalent hydrocarbon group having at least one carbon-carbon triple bond in the middle or at the terminus of the C2-C60 alkyl group, and examples thereof include an ethynyl group and a propynyl group.


The term “C2-C60 alkynylene group” as used herein refers to a divalent group having the same structure as the C2-C60 alkynyl group.


The term “C1-C60 alkoxy group” as used herein refers to a monovalent group represented by —OA101 (wherein A101 is the C1-C60 alkyl group), and examples thereof include a methoxy group, an ethoxy group, and an isopropyloxy group.


The term “C3-C10 cycloalkyl group” as used herein refers to a monovalent saturated hydrocarbon cyclic group having 3 to 10 carbon atoms, and examples thereof are a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group (or bicyclo[2.2.1]heptyl group), a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, and a bicyclo[2.2.2]octyl group.


The term “C3-C10 cycloalkylene group” as used herein refers to a divalent group having the same structure as the C3-C10 cycloalkyl group.


The term “C1-C10 heterocycloalkyl group” as used herein refers to a monovalent cyclic group of 1 to 10 carbon atoms, further including, in addition to carbon atoms, at least one heteroatom, as ring-forming atoms, and specific examples are a 1,2,3,4-oxatriazolidinyl group, a tetrahydrofuranyl group, and a tetrahydrothiophenyl group.


The term “C1-C10 heterocycloalkylene group” as used herein refers to a divalent group having the same structure as the C1-C10 heterocycloalkyl group.


The term “C3-C10 cycloalkenyl group” as used herein refers to a monovalent cyclic group that has 3 to 10 carbon atoms and at least one carbon-carbon double bond in the ring thereof and no aromaticity, and examples thereof include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group.


The term “C3-C10 cycloalkenylene group” as used herein refers to a divalent group having the same structure as the C3-C10 cycloalkenyl group.


The term “C1-C10 heterocycloalkenyl group” as used herein refers to a monovalent cyclic group of 1 to 10 carbon atoms, further including, in addition to carbon atoms, at least one heteroatom, as ring-forming atoms, and having at least one carbon-carbon double bond in the cyclic structure thereof. Examples of the C1-C10 heterocycloalkenyl group include a 4,5-dihydro-1,2,3,4-oxatriazolyl group, a 2,3-dihydrofuranyl group, and a 2,3-dihydrothiophenyl group.


The term “C1-C10 heterocycloalkenylene group” as used herein refers to a divalent group having the same structure as the C1-C10 heterocycloalkenyl group.


The term “C6-C60 aryl group” as used herein refers to a monovalent group having a carbocyclic aromatic system of 6 to 60 carbon atoms.


The term “C6-C60 arylene group” as used herein refers to a divalent group having a carbocyclic aromatic system of 6 to 60 carbon atoms.


Examples of the C6-C60 aryl group are a phenyl group, a pentalenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a heptalenyl group, a naphthacenyl group, a picenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, and an ovalenyl group.


When the C6-C60 aryl group and the C6-C60 arylene group each include two or more rings, the rings may be condensed with each other.


The term “C1-C60 heteroaryl group” as used herein refers to a monovalent group having a heterocyclic aromatic system of 1 to 60 carbon atoms, further including, in addition to carbon atoms, at least one heteroatom, as ring-forming atoms.


The term “C1-C60 heteroarylene group” as used herein refers to a divalent group having a heterocyclic aromatic system of 1 to 60 carbon atoms, further including, in addition to carbon atoms, at least one heteroatom, as ring-forming atoms.


Examples of the C1-C60 heteroaryl group are a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, a benzoquinolinyl group, an isoquinolinyl group, a benzoisoquinolinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, a phenanthrolinyl group, a phthalazinyl group, and a naphthyridinyl group.


When the C1-C60 heteroaryl group and the C1-C60 heteroarylene group each include two or more rings, the rings may be condensed with each other.


The term “monovalent non-aromatic condensed polycyclic group” as used herein refers to a monovalent group (for example, having 8 to 60 carbon atoms) having two or more rings condensed to each other, only carbon atoms as ring-forming atoms, and no aromaticity in its entire molecular structure. Examples of the monovalent non-aromatic condensed polycyclic group are an indenyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, an indenophenanthrenyl group, and an indeno anthracenyl group.


The term “divalent non-aromatic condensed polycyclic group” as used herein refers to a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group described herein.


The term “monovalent non-aromatic condensed heteropolycyclic group” as used herein refers to a monovalent group (for example, having 1 to 60 carbon atoms) having two or more rings condensed to each other, further including, in addition to carbon atoms, at least one heteroatom, as ring-forming atoms, and having non-aromaticity in its entire molecular structure. Examples of the monovalent non-aromatic condensed heteropolycyclic group are a pyrrolyl group, a thiophenyl group, a furanyl group, an indolyl group, a benzoindolyl group, a naphthoindolyl group, an isoindolyl group, a benzoisoindolyl group, a naphthoisoindolyl group, a benzosilolyl group, a benzothiophenyl group, a benzofuranyl group, a carbazolyl group, a dibenzosilolyl group, a dibenzothiophenyl group, a dibenzofuranyl group, an azacarbazolyl group, an azafluorenyl group, an azadibenzosilolyl group, an azadibenzothiophenyl group, an azadibenzofuranyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzopyrazolyl group, a benzimidazolyl group, a benzoxazolyl group, a benzothiazolyl group, a benzoxadiazolyl group, a benzothiadiazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an imidazotriazinyl group, an imidazopyrazinyl group, an imidazopyridazinyl group, an indeno carbazolyl group, an indolocarbazolyl group, a benzofurocarbazolyl group, a benzothienocarbazolyl group, a benzosilolocarbazolyl group, a benzoindolocarbazolyl group, a benzocarbazolyl group, a benzonaphthofuranyl group, a benzonaphthothiophenyl group, a benzonaphtho silolyl group, a benzofurodibenzofuranyl group, a benzofurodibenzothiophenyl group, and a benzothienodibenzothiophenyl group.


The term “divalent non-aromatic condensed heteropolycyclic group” as used herein refers to a divalent group having the same structure as the monovalent non-aromatic condensed heteropolycyclic group described herein.


The term “C6-C60 aryloxy group” as used herein indicates —OA102 (wherein A102 is the C6-C10 aryl group).


The term “C6-C60 arylthio group” as used herein indicates —SA103 (wherein A103 is the C6-C60 aryl group).


The term “C7-C60 arylalkyl group” as used herein refers to -A104A105 (wherein A104 is a C1-C54 alkylene group, and A105 is a C6-C59 aryl group).


The term “C2-C60 heteroarylalkyl group” as used herein refers to -A106A107 (wherein A106 is a C1-C59 alkylene group, and A107 is a C1-C59 heteroaryl group).


The term “R10a” as used herein refers to:

    • deuterium, —F, —CI, —Br, —I, a hydroxyl group, a cyano group, or a nitro group;
    • a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group, each unsubstituted or substituted with deuterium, —F, —CI, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 aryl alkyl group, a C2-C60 heteroaryl alkyl group, —Si(Q11)(Q12)(Q13), —N(Q11)(Q12), —B(Q11)(Q12), —C(═O)(Q11), —S(═O)2(Q11), —P(═O)(Q11)(Q12), or any combination thereof;
    • a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 aryl alkyl group, or a C2-C60 heteroaryl alkyl group, each unsubstituted or substituted with deuterium, —F, —CI, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 aryl alkyl group, a C2-C60 heteroaryl alkyl group, —Si(Q21)(Q22)(Q23), —N(Q21)(Q22), —B(Q21)(Q22), —C(═O)(Q21), —S(═O)2(Q21), —P(═O)(Q21)(Q22), or any combination thereof; or
    • —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), or —P(═O)(Q31)(Q32).


Q1 to Q3, Q11 to Q13, Q21 to Q23 and Q31 to Q33 used herein may each independently be: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; a C1-C60 alkyl group; a C2-C60 alkenyl group; a C2-C60 alkynyl group; a C1-C60 alkoxy group; a C3-C60 carbocyclic group or a C1-C60 heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof; a C7-C60 aryl alkyl group; or a C2-C60 heteroaryl alkyl group.


The term “heteroatom” as used herein refers to any atom other than a carbon atom. Examples of the heteroatom are O, S, N, P, Si, B, Ge, Se, and any combinations thereof.


The term “the third-row transition metal” as used herein includes hafnium (Hf), tantalum (Ta), tungsten (W), rhenium (Re), osmium (Os), iridium (Ir), platinum (Pt), gold (Au), and/or the like.


In the specification, “Ph” refers to a phenyl group, “Me” refers to a methyl group, “Et” refers to an ethyl group, “tert-Bu” or “But” refers to a tert-butyl group, and “OMe” refers to a methoxy group.


The term “biphenyl group” as used herein refers to “a phenyl group substituted with a phenyl group.” For example, the “biphenyl group” is a substituted phenyl group having a C6-C60 aryl group as a substituent.


The term “terphenyl group” as used herein refers to “a phenyl group substituted with a biphenyl group”. For example, the “terphenyl group” is a substituted phenyl group having, as a substituent, a C6-C60 aryl group substituted with a C6-C60 aryl group.


* and *′ as used herein, unless defined otherwise, each refer to a binding site to a neighboring atom in a corresponding formula or moiety.


In the specification, the x-axis, y-axis, and z-axis are not limited to three axes in an orthogonal coordinate system, and may be interpreted in a broad sense including these axes. For example, the x-axis, y-axis, and z-axis may refer to those orthogonal to each other, or may refer to those in different directions that are not orthogonal to each other.


Terms such as “substantially,” “about,” and “approximately” are used as relative terms and not as terms of degree, and are intended to account for the inherent deviations in measured or calculated values that would be recognized by those of ordinary skill in the art. They may be inclusive of the stated value and an acceptable range of deviation as determined by one of ordinary skill in the art, considering the limitations and error associated with measurement of that quantity. For example, “about” may refer to one or more standard deviations, or ±30%, 20%, 10%, 5% of the stated value.


Numerical ranges disclosed herein include and are intended to disclose all subsumed sub-ranges of the same numerical precision. For example, a range of “1.0 to 10.0” includes all subranges having a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as, for example, 2.4 to 7.6. Applicant therefore reserves the right to amend this specification, including the claims, to expressly recite any sub-range subsumed within the ranges expressly recited herein.


The optoelectronic device, the electronic apparatus, and/or any other relevant devices or components according to embodiments of the present disclosure described herein may be implemented utilizing any suitable hardware, firmware (e.g., an application-specific integrated circuit), software, or a combination of software, firmware, and hardware. For example, the various components of the optoelectronic device and/or the electronic apparatus may be formed on one integrated circuit (IC) chip or on separate IC chips. Further, the various components of the optoelectronic device and/or the electronic apparatus may be implemented on a flexible printed circuit film, a tape carrier package (TCP), a printed circuit board (PCB), or formed on one substrate. Further, the various components of the device and/or apparatus may be a process or thread, running on one or more processors, in one or more computing devices, executing computer program instructions and interacting with other system components for performing the various functionalities described herein. The computer program instructions are stored in a memory which may be implemented in a computing device using a standard memory device, such as, for example, a random access memory (RAM). The computer program instructions may also be stored in other non-transitory computer readable media such as, for example, a CD-ROM, flash drive, or the like. Also, a person of skill in the art should recognize that the functionality of various computing devices may be combined or integrated into a single computing device, or the functionality of a particular computing device may be distributed across one or more other computing devices without departing from the scope of the embodiments of the present disclosure.


Hereinafter, compounds according to one or more embodiments and light-emitting devices according to one or more embodiments will be described in more detail with reference to the following synthesis examples and examples. The wording “B was used instead of A” used in describing Synthesis Examples refers to that an substantially identical molar equivalent of B was used in place of A.


EXAMPLES
Synthesis Example 1-1 (Synthesis of Compound P1)



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2,3,7,8-tetrabromo-5,5-difluoro-10-phenyl-5H-414,514-dipyrrolo[1,2-c:2′,1′-f][1,3,2]diazaborinine, phenylboronic acid, Pd(PPh3)4, and Na2CO3 were added to toluene and stirred at 110° C. for 8 hours. An organic layer was obtained by extraction using dichloromethane that was washed with a sodium chloride aqueous solution and then dried by adding MgSO4 thereto. An obtained product was subjected to separation and purification through silica gel chromatography to obtain Compound P1 (5,5-difluoro-2,3,7,8,10-pentaphenyl-5H-414,514-dipyrrolo[1,2-c:2′,1′-f][1,3,2]diazaborinine). Compound P1 thus obtained was identified by 1H NMR (CDCl3, 500 MHz) and MS/FAB.


Compound P1: (500 MHz, CDCl3): 7.84 (m, 2H), 7.51 (m, 3H), 7.43 (m, 4H), 7.34 (m, 10H), 7.18 (m, 6H), 7.02 (s, 2H)


Compound P1: C39H27BF2N2: calc. 572.47, found 572.22 Synthesis Example 1-2 (Synthesis of Compound P2)




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Compound P2 (5,5-difluoro-3,7-dimethyl-2,8,10-triphenyl-5H-414,514-dipyrrolo[1,2-c:2′,1′-f][1,3,2]diazaborinine) was synthesized in substantially the same manner as in Synthesis Example 1-1, except that in the synthesis process of Synthesis Example 1-1, 2,8-dibromo-5,5-difluoro-3,7-dimethyl-10-phenyl-5H-414,514-dipyrrolo[1,2-c:2′,1′-f][1,3,2]diazaborinine was used instead of 2,3,7,8-tetrabromo-5,5-difluoro-10-phenyl-5H-414,514-dipyrrolo[1,2-c:2′,1′-f][1,3,2]diazaborinine. Compound P2 thus obtained was identified by 1H NMR (CDCl3, 500 MHz) and MS/FAB.


Compound P2: (500 MHz, CDCl3): 7.51 (m, 2H), 7.44 (m, 3H), 7.36 (m, 8H), 7.17 (m, 2H), 7.02 (s, 2H), 2.12 (s, 6H)


Compound P2: C39H23BF2N2: calc. 448.32, found 448.19


Synthesis Example 1-3 (Synthesis of Compound P3)



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Compound P3 (5,5-difluoro-2,8-dimethyl-3,7,10-triphenyl-5H-414,514-dipyrrolo[1,2-c:2′,1′-f][1,3,2]diazaborinine) was synthesized in substantially the same manner as in Synthesis Example 1-1, except that in the synthesis process of Synthesis Example 1-1, 3,7-dibromo-5,5-difluoro-2,8-dimethyl-10-phenyl-5H-414,514-dipyrrolo[1,2-c:2′,1′-f][1,3,2]diazaborinine was used instead of 2,3,7,8-tetrabromo-5,5-difluoro-10-phenyl-5H-414,514-dipyrrolo[1,2-c:2′,1′-f][1,3,2]diazaborinine. Compound P3 thus obtained was identified by 1H NMR (CDCl3, 500 MHz) and MS/FAB.


Compound P3: (500 MHz, CDCl3): 7.84 (m, 2H), 7.52 (m, 3H), 7.43 (m, 3H), 7.34 (m, 7H), 6.46 (s, 2H), 2.12 (s, 6H)


Compound P3: C39H23BF2N2: calc. 448.32, found 448.19


Synthesis Example 2-1 (Synthesis of Compound N1)



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Compound N1 (Naphthalene-1,4,5,8-Tetracarboxylic Dianhydride)

Compound N1 was used after sublimation purification by using a commercialized material (CAS Nnumber: 81-30-1). Compound N1 was identified by 1H NMR (CDCl3, 500 MHz) and MS/FAB.


Compound N1: (500 MHz, CDCl3): 9.05 (s, 4H)


Compound N1: C14H4O6: calc. 268.18, found 268.00


Synthesis Example 2-2 (Synthesis of Compound N5)



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Compound N1 and aniline were dissolved in dimethylformamide and stirred at 150° C. for 8 hours. After cooling a reaction solution to room temperature, an organic layer was obtained by extraction with ethyl acetate that was dried by using MgSO4, and the residue obtained by evaporating a solvent was subjected to separation and purification through silica gel chromatography to obtain Compound N5 (2,7-diphenylbenzo[Imn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone). Compound N5 thus obtained was identified by 1H NMR (CDCls, 500 MHz) and MS/FAB.


Compound N5: (500 MHz, CDCls): δ 8.62 (s, 4H), 7.58 (m, 6H), 7.43 (m, 4H)


Compound N5: C26H14N2O4: calc. 418.41, found 418.10


Synthesis Example 2-3 (Synthesis of Compound N9)



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Compound N9 (4,4′-(1,3,6,8-tetraoxo-1,3,6,8-tetrahydrobenzo[Imn][3,8]phenanthroline-2,7-diyl)dibenzonitrile) was synthesized in substantially the same manner as in the synthesis of Compound N5, except that in the synthesis process of Synthesis Example 2-2, 4-aminobenzonitrile was used instead of aniline. Compound N9 thus obtained was identified by 1H NMR (CDCls, 500 MHz) and MS/FAB.


Compound N9: (500 MHz, CDCl3): δ 8.62 (s, 4H), 7.83 (m, 4H), 7.62 (m, 4H)


Compound N9: C28H12N4O4: calc. 468.43, found 468.09


Synthesis Example 3-1 (Synthesis of Compound 1)



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2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine, 2-(9,9-dimethyl-9H-fluoren-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, Pd(PPh3)4, and K2CO3 were added to 1,4-dioxane and stirred at 100° C. for 8 hours. An organic layer was obtained by extraction using ethyl acetate that was washed by using a sodium chloride aqueous solution and then dried by adding MgSO4 thereto. An obtained product was subjected to separation and purification through silica gel chromatography to obtain Compound 1 (2-(4-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)-4,6-diphenyl-1,3,5-triazine). Compound 1 thus obtained was identified by 1H NMR (CDCl3, 500 MHz) and MS/FAB.


Compound 1: (500 MHz, CDCl3): 8.36 (m, 4H), 8.00˜7.80 (m, 6H), 7.50 (m, 7H), 7.40˜7.25 (m, 4H), 1.69 (s, 6H)


Compound 1: C36H27N3: calc. 501.63, found 501.22


Synthesis Example 3-2 (Synthesis of Compound 2)



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Compound 2 (2-(4-(9,9-dimethyl-9H-fluoren-3-yl)phenyl)-4,6-diphenyl-1,3,5-triazine) was synthesized in substantially the same manner as in the synthesis of Compound 1, except that in the synthesis process of Synthesis Example 3-1, 2-(9,9-dimethyl-9H-fluoren-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was used instead of 2-(9,9-dimethyl-9H-fluoren-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane. Compound 2 thus obtained was identified by 1H NMR (CDCl3, 500 MHz) and MS/FAB.


Compound 2: (500 MHz, CDCl3): 8.36 (m, 4H), 8.18˜7.70 (m, 6H), 7.50 (m, 7H), 7.40˜7.25 (m, 4H), 1.69 (s, 6H)


Compound 2: C36H27N3: calc. 501.63, found 501.22


Synthesis Example 3-3 (Synthesis of Compound 3)



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Compound 3 (2-(4-(9,9-dimethyl-9H-fluoren-4-yl)phenyl)-4,6-diphenyl-1,3,5-triazine) was synthesized in substantially the same manner as in the synthesis of Compound 1, except that in the synthesis process of Synthesis Example 3-1, 2-(9,9-dimethyl-9H-fluoren-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was used instead of 2-(9,9-dimethyl-9H-fluoren-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane. Compound 3 thus obtained was identified by 1H NMR (CDCl3, 500 MHz) and MS/FAB.


Compound 3: (500 MHz, CDCl3): 8.36 (m, 4H), 8.00-7.60 (m, 6H), 7.50 (m, 7H), 7.40-7.25 (m, 4H), 1.69 (s, 6H)


Compound 3: C36H27N3: calc. 501.63, found 501.22


Synthesis Example 3-4 (Synthesis of Compound 5)



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Compound 5 (2-(4-(9,9-diphenyl-9H-fluoren-3-yl)phenyl)-4,6-diphenyl-1,3,5-triazine) was synthesized in substantially the same manner as in the synthesis of Compound 1, except that in the synthesis process of Synthesis Example 3-1, 2-(9,9-diphenyl-9H-fluoren-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was used instead of 2-(9,9-dimethyl-9H-fluoren-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane. Compound 5 thus obtained was identified by 1H NMR (CDCl3, 500 MHz) and MS/FAB.


Compound 5: (500 MHz, CDCl3): 8.36 (m, 4H), 8.00-7.60 (m, 6H), 7.50 (m, 7H), 7.40-7.10 (m, 14H)


Compound 5: C46H31N3: calc. 625.78, found 625.25 Example 1


As an anode, a glass substrate (product of Corning Inc.) with a 15 ohm per square centimeter (Ω/cm2) (1,200 angstrom (Å)) ITO formed thereon was cut to a size of 50 millimeter (mm)×50 mm×0.7 mm, sonicated by using isopropyl alcohol and pure water each for 5 minutes, washed by irradiation of ultraviolet rays and exposure of ozone thereto for 30 minutes, and then mounted on a vacuum deposition apparatus.


2-TNATA was vacuum deposited on the anode to form a hole injection layer having a thickness of 100 Å. 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter, NPB) was vacuum deposited on the hole injection layer to form a hole transport layer having a thickness of 1,250 Å.


Compound P1 was vacuum-deposited on the hole transport layer to form a first layer having a thickness of 100 Å. Compound N1 was vacuum-deposited on the first layer to form a second layer having a thickness of 350 Å. Compound 1 was vacuum-deposited on the second layer to form a buffer layer having a thickness of 50 Å.


Compound ET1 was vacuum-deposited on the buffer layer to form an electron transport layer having a thickness of 300 Å. LiQ was vacuum deposited on the electron transport layer to form an electron injection layer having a thickness of 10 Å. AgMg was vacuum deposited on the electron injection layer to form a cathode having a thickness of 100 Å, thereby completing manufacture of an optoelectronic device.




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Examples 2 and 3 and Comparative Examples 1 to 14

Optoelectronic devices were manufactured in substantially the same manner as in Example 1, except that the compounds shown in Table 1 were each used instead of Compound P1 in forming the first layer included in the optical activation layer, the compounds shown in Table 1 were each used instead of Compound N1 in forming the second layer included in the optical activation layer, and the compounds shown in Table 1 were each used instead of Compound 1 in forming the buffer layer. Compound A1 indicated in Table 1 may be referred to as SubPC, Compound A2 may be referred to as SubNC, and Compound B1 may be referred to as fullerene 60.


Evaluation Example 1

To evaluate the performance characteristics of the optoelectronic devices manufactured in Examples 1 to 3 and Comparative Examples 1 to 14, external quantum efficiency (EQE) was measured, and results thereof are shown in Table 1. The EQE refers to a ratio of electrical energy generated from energy of irradiated light.


Light with a wavelength of 530 nanometer (nm) was irradiated to the optoelectronic device by using an external quantum efficiency measuring device (K3100, McScience, Korea). Current generated during light irradiation was measured by using a current meter (Keithley, Tektronix, USA). The EQE was calculated by using the irradiated light and the measured current.













TABLE 1






First
Second
Third




compound
compound
compound
EQE (%)



















Example 1
Compound P1
Compound N1
Compound 1
25.3


Example 2
Compound P2
Compound N5
Compound 2
32.1


Example 3
Compound P3
Compound N9
Compound 3
29.4


Comparative
A1
B1
Py-1
0.9


Example 1






Comparative
A1
B1
Py-2
1.2


Example 2






Comparative
A1
B1
Compound 1
0.6


Example 3






Comparative
A2
Compound N1
Compound 1
2.8


Example 4






Comparative
A2
Compound N5
Compound 2
3.1


Example 5






Comparative
A2
B1
Compound 5
5.7


Example 6






Comparative
Compound P1
Compound N1
Py-1
7.5


Example 7






Comparative
Compound P2
Compound N5
Py-2
6.2


Example 8






Comparative
Compound P3
Compound N9
Py-3
7.4


Example 9






Comparative
Compound P1
Compound N1
C4
7.5


Example 10






Comparative
Compound P2
Compound N5
C5
6.2


Example 11






Comparative
Compound P3
Compound N9
C6
7.4


Example 12






Comparative
Compound P1
Compound N1
C7
3.5


Example 13






Comparative
Compound P2
Compound N5
C8
4.8


Example 14







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From Table 1, it is confirmed that the optoelectronic devices of Examples 1 to 3 each had higher EQE than the optoelectronic devices of Comparative Examples 1 to 14.


The optoelectronic device which includes, in the optical activation layer, the first compound and the second compound and includes in the buffer layer the third compound may (e.g., should) have high EQE. Accordingly, an electronic apparatus including the optoelectronic device may have improved quality.


It should be understood that embodiments described herein should be considered in a descriptive sense only and not for purposes of limitation. Descriptions of features or aspects within each embodiment should typically be considered as available for other similar features or aspects in one or more embodiments. While one or more embodiments have been described with reference to the drawings, it will be understood by those of ordinary skill in the art that one or more suitable changes in form and details may be made therein without departing from the spirit and scope as defined by the following claims, and equivalents thereof.

Claims
  • 1. An optoelectronic device comprising: a first electrode;a second electrode opposite to the first electrode;an optical activation layer between the first electrode and the second electrode; anda buffer layer between the optical activation layer and the second electrode,the optical activation layer comprising a first compound represented by Formula 1 and a second compound represented by Formula 2, andthe buffer layer comprising a third compound represented by Formula 3:
  • 2. The optoelectronic device of claim 1, wherein the optical activation layer excludes at least one selected from among a fullerene-based compound, a phthalocyanine-based compound, and a subphthalocyanine-based compound.
  • 3. The optoelectronic device of claim 1, wherein an absolute value of a lowest unoccupied molecular orbital energy level of the third compound is about 2.0 electron volt (eV) to about 2.5 eV.
  • 4. The optoelectronic device of claim 1, wherein an absolute value of a highest occupied molecular orbital energy level of the third compound is about 5.0 eV to about 7.0 eV.
  • 5. The optoelectronic device of claim 1, wherein, in Formula 1, X11 is C(R11), X12 is C(R12), X13 is C(R13), X14 is C(R14), X15 is C(R15), X16 is C(R16), and X17 is C(R17).
  • 6. The optoelectronic device of claim 1, wherein R11 to R17 are each independently: hydrogen, deuterium, —F, —Cl, or a cyano group;a C1-C30 alkyl group or a C1-C30 alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, a cyano group, or any combination thereof; ora C3-C30 aryl group or a C1-C30 heteroaryl group, each unsubstituted or substituted with deuterium, —F, —Cl, a cyano group, —CF3, a C1-C10 alkoxy group, or any combination thereof.
  • 7. The optoelectronic device of claim 1, wherein, in Formula 1, R18 and R19 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, or a cyano group.
  • 8. The optoelectronic device of claim 1, wherein the first compound is represented by any one selected from among Formulae 1A to 1E:
  • 9. The optoelectronic device of claim 1, wherein, in Formula 2, X21 to X24 are each independently O or S.
  • 10. The optoelectronic device of claim 1, wherein, in Formula 2, Z21 and Z22 are each independently O or N(R4), and R4 is:hydrogen, deuterium, —F, —Cl, or a cyano group;a C1-C30 alkyl group or a C1-C30 alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, a cyano group, or any combination thereof; ora C3-C30 carbocyclic group or a C1-C30 heterocyclic group, each unsubstituted or substituted with deuterium, —F, —Cl, a cyano group, —CF3, a C1-C10 alkoxy group, or any combination thereof.
  • 11. The optoelectronic device of claim 1, wherein, in Formula 2, Ar21 is a phenyl group unsubstituted or substituted with at least one R10a, a biphenyl group unsubstituted or substituted with at least one R10a, a naphthalene group unsubstituted or substituted with at least one R10a, or a phenylene group unsubstituted or substituted with at least one R10a.
  • 12. The optoelectronic device of claim 1, wherein the second compound is represented by any one selected from among Formulae 2A to 2F:
  • 13. The optoelectronic device of claim 1, wherein, in Formula 3, Ar31 to Ar33 are each independently a benzene group unsubstituted or substituted with at least one R10a, a naphthalene group unsubstituted or substituted with at least one R10a, a fluorene group unsubstituted or substituted with at least one R10a, or a spiro-bifluorene group unsubstituted or substituted with at least one R10a.
  • 14. The optoelectronic device of claim 1, wherein, in Formula 3, Ar31 to Ar33 are each independently represented by any one selected from among Formulae 3-1 to 3-11:
  • 15. The optoelectronic device of claim 1, wherein, in Formula 3, L31 to L33 are each independently a single bond, a phenyl group unsubstituted or substituted with at least one R10a, or a naphthalene group unsubstituted or substituted with at least one R10a.
  • 16. The optoelectronic device of claim 1, wherein, in Formula 3, L31 to L33 are each independently a single bond or a group represented by any one selected from among Formulae 4-1 to 4-49:
  • 17. The optoelectronic device of claim 1, wherein the first compound is any one selected from among Compounds P1 to P102:
  • 18. The optoelectronic device of claim 1, wherein the second compound is any one selected from among Compounds N1 to N43:
  • 19. The optoelectronic device of claim 1, wherein the third compound is any one selected from among Compounds 1 to 148:
  • 20. An electronic apparatus comprising the optoelectronic device of claim 1.
Priority Claims (1)
Number Date Country Kind
10-2024-0010149 Jan 2024 KR national