ORGANIC COMPOUND, OPTO-ELECTRONIC DEVICE INCLUDING THE SAME, ELECTRONIC APPARATUS INCLUDING THE OPTO-ELECTRONIC DEVICE, AND ELECTRONIC DEVICE INCLUDING THE ELECTRONIC APPARATUS

Information

  • Patent Application
  • 20240099134
  • Publication Number
    20240099134
  • Date Filed
    August 30, 2023
    9 months ago
  • Date Published
    March 21, 2024
    2 months ago
Abstract
An opto-electronic device may include a first electrode, a second electrode facing the first electrode, a photoactive layer between the first electrode and the second electrode, and an organic compound represented by Formula 1, wherein, in Formula 1, CY1 is a group represented by Formula 2, and CY2 is a group represented by Formula 3.
Description
CROSS-REFERENCE TO RELATED APPLICATION

This application claims priority to and the benefit of Korean Patent Application No. 10-2022-0110320, filed on Aug. 31, 2022, in the Korean Intellectual Property Office, the content of which is incorporated by reference herein in its entirety.


BACKGROUND
1. Field

One or more embodiments of the present disclosure relate to an organic compound, an opto-electronic device including the same, an electronic apparatus including the opto-electronic device, and an electronic device including the electronic apparatus.


2. Description of the Related Art

Opto-electronic devices are devices that convert light energy or a light signal into electrical energy or an electrical signal. Examples of the opto-electronic devices include a photovoltaic cell or a solar cell that converts light energy into electrical energy, a photodetector or a light sensor that detects light energy and converts the detected light energy into an electrical signal, and/or the like.


Electronic apparatuses including opto-electronic devices and organic light-emitting devices have been developed and utilized. For example, light emitted from an organic light-emitting device may be reflected by an object (e.g., a finger of a user) in contact with an electronic apparatus to be incident on an opto-electronic device. As the opto-electronic device detects incident light energy and converts the detected incident light energy into an electrical signal, it may be recognized that the object is in contact with the electronic apparatus. The opto-electronic device may be utilized as a fingerprint recognition sensor and/or the like.


SUMMARY

One or more aspects of embodiments of the present disclosure are directed toward an organic compound having improved light absorption efficiency for a specific wavelength, and an opto-electronic device having high light absorption efficiency by including the organic compound.


One or more aspects of embodiments of the present disclosure are directed toward a high-quality electronic apparatus including the opto-electronic device and a high-quality electronic device including the electronic apparatus.


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 of the present disclosure, an opto-electronic device may include a first electrode, a second electrode facing the first electrode, a photoactive layer between the first electrode and the second electrode, and an organic compound represented by Formula 1




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    • wherein, in Formulae 1 to 3,

    • CY1 may be a group represented by Formula 2,

    • CY2 may be a group represented by Formula 3,

    • X1 and X2 may each independently be O, S, or Se,

    • *1 and *2 may each be a binding site to CY1,

    • *3 and *4 may each be a binding site to CY2,

    • T1 may be *-(L1)b1-(R1)c1,

    • T2 may be *-(L2)b2-(R2)c2,

    • a1 and a2 may each independently be an integer from 0 to 2,

    • L1 and L2 may each independently be a single bond, a C5-C30 carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C30 heterocyclic group unsubstituted or substituted with at least one R10a,

    • b1 and b2 may each independently be an integer from 0 to 3,

    • R1, R2, Z1, and Z2 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, —OH, —CN, —NO2, —CF3, 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, —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —C(═O)O(Q1), —S(═O)2(Q1), or —P(═O)(Q1)(Q2),

    • at least one selected from among Z1 and Z2 may be selected from among a π electron-deficient nitrogen-containing ring, —F, —Cl, —Br, —I, —CF3, —OH, —NO2, —CN, and a C1-C60 alkyl group substituted with at least one selected from —F, —Cl, —Br, —I, —CF3, —NO2, and —CN,

    • c1 and c2 may each independently be an integer from 0 to 10,

    • 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 arylalkyl group, a C2-C60 heteroarylalkyl 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 arylalkyl group, or a C2-C60 heteroarylalkyl 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 arylalkyl group, a C2-C60 heteroarylalkyl 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; 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 arylalkyl group; or a C2-C60 heteroarylalkyl group.





According to one or more embodiments of the present disclosure, an electronic apparatus may include the opto-electronic device.


According to one or more embodiments of the present disclosure, an electronic device may include the electronic apparatus.


According to one or more embodiments of the present disclosure, provided is the organic compound represented by Formula 1.





BRIEF DESCRIPTION OF THE DRAWINGS

The accompanying drawings are included to provide a further understanding of the present disclosure and are incorporated in and constitute a part of the present disclosure. The drawings illustrate embodiments of the present disclosure and, together with the description, serve to explain principles of the present disclosure. The above and other aspects, features, and advantages of certain embodiments of the disclosure will be more apparent from the following description taken in conjunction with the accompanying drawings, in which:



FIG. 1 is a schematic view of an opto-electronic device according to one or more embodiments of the present disclosure;



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



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



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



FIG. 5 is a schematic perspective view of an electronic device including a light-emitting device according to one or more embodiments of the present disclosure;



FIG. 6 is a schematic view of the exterior of a vehicle as an electronic device including a light-emitting device according to one or more embodiments of the present disclosure; and



FIGS. 7A-7C are schematic views of the interior of a vehicle according to one or more embodiments of the present disclosure.





DETAILED DESCRIPTION

Reference will now be made in more detail to embodiments, examples of which are illustrated in the accompanying drawings, wherein like reference numerals refer to like elements throughout the present disclosure, and duplicative descriptions thereof may not be provided for conciseness. In this regard, the embodiments of the present disclosure may have different forms and should not be construed as being limited to the descriptions set forth herein. Accordingly, the embodiments of the present disclosure are merely described, by referring to the drawings, to explain aspects of the present disclosure. As utilized herein, the term “and/or” or “or” includes any and all combinations of one or more of the associated listed items. Throughout the disclosure, the expression “at least one of a, b and 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.


One or more aspects of embodiments of the present disclosure are directed to an opto-electronic device including a first electrode, a second electrode facing the first electrode, a photoactive layer between the first electrode and the second electrode, and an organic compound represented by Formula 1.


In one or more embodiments, the first electrode may be an anode, and the second electrode may be a cathode. The photoactive layer may include an organic compound, and may be to absorb light. The organic compound is the same as described herein.


In one or more embodiments, the opto-electronic device may further include a hole transport region between the first electrode and the photoactive layer and an electron transport region between the photoactive layer and the second electrode. The photoactive layer may include the organic compound.


In one or more embodiments, the photoactive layer may include a first layer adjacent to the hole transport region and a second layer adjacent to the electron transport region. The second layer may include the organic compound.


For example, in some embodiments, the first layer may include a donor compound, the second layer may include an acceptor compound, and the acceptor compound may be the organic compound.


For example, in some embodiments, the donor compound may be to absorb light. As the donor compound absorbs light, electrons at a highest occupied molecular orbital (HOMO) energy level in the donor compound may be transferred to a lowest unoccupied molecular orbital (LUMO) energy level in the donor compound to form excitons. The excitons may move to an interface between the first layer and the second layer within the first layer, and then may provide electrons to a LUMO energy level of the acceptor compound. An electron-hole pair may be formed at the interface. The acceptor compound may separate electrons and holes, and the separated electrons and holes may move to the electron transport region and the hole transport region, respectively.


In one or more embodiments, the LUMO energy level of the acceptor compound included in the second layer may be lower than the LUMO energy level of the donor compound included in the first layer.


In one or more embodiments, an absolute value of the LUMO energy level of the acceptor compound included in the second layer may be greater than 3.66 eV. For example, the absolute value of the LUMO energy level of the acceptor compound included in the second layer may be equal to or greater than 4.0 eV.


For example, in some embodiments, the first layer may include boron subphthalocyanine chloride (SubPC).


For example, in some embodiments, the first layer may be referred to as a P-type or kind layer or an electron donor layer. The second layer may be referred to as an N-type or kind layer or an electron acceptor layer.


In one or more embodiments, the first layer may be in direct contact with the hole transport region. The second layer may be in direct contact with the electron transport region.


One or more aspects of embodiments of the present disclosure are directed to an electronic apparatus including the opto-electronic 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 between the first electrode and the second electrode and not overlapping the photoactive layer, and a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or any combination thereof.


For example, in some embodiments, a light-emitting device may include the first electrode, the emission layer, and the second electrode. The light-emitting device may further include a hole transport region between the first electrode and the emission layer and overlapping the emission layer, and an electron transport region between the second electrode and the emission layer and overlapping the emission layer.


In some embodiments, each of the hole transport region and the electron transport region may be a common layer, and may overlap both (e.g., simultaneously) the photoactive layer and the emission layer.


In one or more embodiments, 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. The electron transport region may include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.


One or more aspects of embodiments of the present disclosure are directed to an electronic device including the electronic apparatus. The electronic device may be one or more selected from among a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor or outdoor lighting and/or signal light, 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 microdisplay, a three-dimensional (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.


One or more aspects of embodiments of the present disclosure are directed to an organic compound represented by Formula 1:




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In Formulae 1 to 3,

    • CY1 may be a group represented by Formula 2,
    • CY2 may be a group represented by Formula 3,
    • X1 and X2 may each independently be O, S, or Se,
    • *1 and *2 may each be a binding site to CY1,
    • *3 and *4 may each be a binding site to CY2,
    • T1 may be *-(L1)b1-(R1)c1,
    • T2 may be *-(L2)b2-(R2)c2,
    • a1 and a2 may each independently be an integer from 0 to 2,
    • L1 and L2 may each independently be a single bond, a C5-C30 carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C30 heterocyclic group unsubstituted or substituted with at least one R10a,
    • b1 and b2 may each independently be an integer from 0 to 3,
    • R1, R2, Z1, and Z2 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, —OH, —CN, —NO2, —CF3, 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-C0 arylalkyl group unsubstituted or substituted with at least one R10a, a C2-C60 heteroarylalkyl group unsubstituted or substituted with at least one R10a, —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —C(═O)O(Q1), —S(═O)2(Q1), or —P(═O)(Q1)(Q2),
    • at least one selected from among Z1 and Z2 may be selected from: a π electron-deficient nitrogen-containing ring, —F, —Cl, —Br, —I, —CF3, —OH, —NO2, —CN, and a C1-C60 alkyl group substituted with at least one selected from —F, —Cl, —Br, —I, —CF3, —NO2, and —CN,
    • c1 and c2 may each independently be an integer from 0 to 10,
    • 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 arylalkyl group, a C2-C60 heteroarylalkyl 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 arylalkyl group, or a C2-C60 heteroarylalkyl 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 arylalkyl group, a C2-C60 heteroarylalkyl 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; 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 arylalkyl group; or a C2-C60 heteroarylalkyl group.


In one or more embodiments, the organic compound may be represented by one selected from among Formulae 2-1 to 2-3:




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In Formulae 2-1 to 2-3,

    • T11 to T13 may each be the same as described herein with respect to T1, and
    • CY2, X1, T2, Z1, Z2, and a2 may each be the same as described herein.


For example, in some embodiments, the organic compound may be represented by Formula 2-1.


In one or more embodiments, the organic compound may be represented by one selected from among Formulae 3-1 to 3-9:




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In Formulae 3-1 to 3-9,

    • T11 to T13 may each be the same as described herein with respect to T1,
    • T21 to T23 may each be the same as described herein with respect to T2, and
    • X1, X2, Z1, and Z2 may each be the same as described herein.


For example, in some embodiments, the organic compound may be represented by Formula 3-1.


In one or more embodiments, X1 and X2 in Formulae 1 to 3 may each independently be S or Se.


In one or more embodiments, X1 and X2 in Formulae 1 to 3 may be identical to each other.


In one or more embodiments, L1 and L2 in Formulae 1 to 3 may each independently be a single bond or a C1-C30 heterocyclic group unsubstituted or substituted with at least one R10a.


For example, in some embodiments, L1 and L2 in Formulae 1 to 3 may each independently be a single bond, a 5-membered or 6-membered monocyclic group (e.g., monoheterocyclic group) unsubstituted or substituted with at least one R10a, or a condensed heterocyclic group in which two or three 5-membered or 6-membered monocyclic groups (e.g., monoheterocyclic groups), each unsubstituted or substituted with at least one R10a, are condensed together.


For example, in some embodiments, the 5-membered or 6-membered monocyclic group may be a cyclopentane group, a cyclohexane group, a pyrrole group, a furan group, a thiophene group, a pyridine group, a pyrazine group, a pyrimidine group, or a pyridazine group.


For example, in some embodiments, the 5-membered or 6-membered monocyclic group may be a cyclopentane group, a cyclohexane group, a pyrrole group, a furan group, a thiophene group, a thiophenedioxide group, a tetrahydrofuran group, a tetrahydrothiophene group, a benzene group, a pyridine group, a pyrazine group, a pyrimidine group, or a pyridazine group.


In one or more embodiments, L1 and L2 in Formulae 1 to 3 may each independently be: a single bond,

    • a pyrrolylene group, a furanylene group, a thiophenylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a quinolinylene group, an isoquinolinylene group, a 4,6-dimethylene-5,6-dihydro-4H-cyclopentathiophenylene group, a benzofuranylene group, a benzothiophenylene group, a thienofuranylene group, a thienothiophenylene group, a thienofurandionylene group, a thienothiophenedionylene group, a thienothiophenedioxydylene group, a benzodifurantetraonylene group, or a naphthyridinylene group; or
    • a pyrrolylene group, a furanylene group, a thiophenylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a quinolinylene group, an isoquinolinylene group, a 4,6-dimethylene-5,6-dihydro-4H-cyclopentathiophenylene group, a benzofuranylene group, a benzothiophenylene group, a thienofuranylene group, a thienothiophenylene group, a thienofurandionylene group, a thienothiophenedionylene group, a thienothiophenedioxydylene group, a benzodifurantetraonylene group, or a naphthyridinylene group, each substituted with: —F, —Cl, —Br, —I, —CF3, —NO2, or —CN; a C1-C60 alkyl group unsubstituted or substituted with —F, —Cl, —Br, —I, —CF3, —NO2, or —CN; or a pyrrolyl group, a furanyl group, a thiophenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a 4,6-dimethylene-5,6-dihydro-4H-cyclopentathiophenyl group, a benzofuranyl group, a benzothiophenyl group, a thienofuranyl group, a thienothiophenyl group, a thienofurandionyl group, a thienothiophenedionyl group, a thienothiophenedioxydyl group, a benzodifurantetraonyl group, or a naphthyridinyl group.


In one or more embodiments, L1 and L2 in Formulae 1 to 3 may each independently be: a thiophenylene group, a 4,6-dimethylene-5,6-dihydro-4H-cyclopentathiophenylene group, a benzofuranylene group, a benzothiophenylene group, a thienofuranylene group, a thienothiophenylene group, a thienofurandionylene group, a thienothiophenedionylene group, a thienothiophenedioxydylene group, a benzodifurantetraonylene group, or a naphthyridinylene group; or

    • a thiophenylene group, a 4,6-dimethylene-5,6-dihydro-4H-cyclopentathiophenylene group, a benzofuranylene group, a benzothiophenylene group, a thienofuranylene group, a thienothiophenylene group, a thienofurandionylene group, a thienothiophenedionylene group, a thienothiophenedioxydylene group, a benzodifurantetraonylene group, or a naphthyridinylene group, each substituted with: —F, —Cl, —Br, —I, —CF3, —NO2, or —CN; or a C1-C12 alkyl group.


In one or more embodiments, b1 and b2 in Formula 1 may each independently be 0 or 1.


In one or more embodiments, the sum of b1 and b2 in Formula 1 may be an integer of 1 or more. For example, in some embodiments, the sum of b1 and b2 in Formulae 1 to 3 may be 1 or 2.


In one or more embodiments, R1, R2, Z1, and Z2 in Formulae 1 to 3 may each independently be: hydrogen, deuterium, —F, —Cl, —Br, —I, —OH, —CN, —NO2, —CF3, a C1-C60 alkyl group unsubstituted or substituted with at least one R10a, or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a; or —C(═O)(Q1) or —C(═O)O(Q1).


In one or more embodiments, R1, R2, Z1, and Z2 may each independently be: hydrogen, —F, —Cl, —Br, —I, —OH, —CN, —NO2, —CF3, or a C1-C12 alkyl group; or —C(═O)(Q1) or —C(═O)O(Q1).


In one or more embodiments, at least one selected from among R1 and R2 in Formulae 1 to 3 may be: —F, —Cl, —Br, —I, —CN, —CF3, or a C1-C12 alkyl group; or —C(═O)(Q1) or —C(═O)O(Q1).


In one or more embodiments, the sum of c1 and c2 in Formulae 1 to 3 may be an integer of 1 or more. For example, in some embodiments, the sum of c1 and c2 in Formulae 1 to 3 may be an integer of 2 or more.


In one or more embodiments, at least one selected from among Z1 and Z2 in Formulae 1 to 3 may be —F, —Cl, —Br, —I, —OH, —CN, —NO2, or —CF3.


In one or more embodiments, Z1 and Z2 in Formulae 1 to 3 may be identical to each other. In one or more embodiments, Z1 and Z2 in Formulae 1 to 3 may be different from each other.


In one or more embodiments, Z1 and Z2 in Formulae 1 to 3 may each be —CN.


In one or more embodiments, the organic compound may have a plane symmetric structure.


In one or more embodiments, the organic compound may be one selected from among Compounds 1 to 24:




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Because the organic compound is represented by the structure represented by Formula 1, the organic compound may have a low LUMO energy level, and may also have high electron affinity characteristics by including an electron withdrawing group (EWG). As a result, the organic compound may have excellent or suitable stability in a negatively charged state, thereby having an improved degree of separation between electrons and holes. Accordingly, an opto-electronic device including the organic compound may have improved energy efficiency.


Descriptions of FIGS. 1 and 2


FIG. 1 is a schematic view of an opto-electronic device 30 according to one or more embodiments of the present disclosure. The opto-electronic device 30 may include a first electrode 110, a hole transport region 120, a photoactive layer 135, an electron transport region 140, and a second electrode 150.



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


Hereinafter, the structures of the opto-electronic device 30 and the light-emitting device 10 according to embodiments and methods of manufacturing the opto-electronic device 30 and the light-emitting device 10 will be described with reference to FIGS. 1 and 2.


First Electrode 110

In FIG. 1 and FIG. 2, a substrate may be additionally arranged/provided under the first electrode 110 or on the second electrode 150. As the substrate, a glass substrate or a plastic substrate may be utilized. In one or more embodiments, the substrate may be a flexible substrate, and 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, for example, depositing or sputtering a material for forming the first electrode 110 on the substrate. When the first electrode 110 is an anode, a material for forming the first electrode 110 may be a high-work function material that facilitates injection of holes.


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


The first electrode 110 may have a single-layered structure including (e.g., consisting of) a single layer or a multi-layered structure including a plurality of layers. For example, in some embodiments, the first electrode 110 may have a three-layered structure of ITO/Ag/ITO.


Hole Transport Region 120

The hole transport region 120 may have: i) a single-layered structure including (e.g., consisting of) a single layer including (e.g., consisting of) a single material; ii) a single-layered structure including (e.g., consisting of) a single layer including (e.g., consisting of) a plurality of different materials; or iii) a multi-layered structure including a plurality of layers including different materials.


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, in some embodiments, the hole transport region 120 may have a multi-layered 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 in the stated order.


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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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 R11a, or a C2-C5 alkenylene group unsubstituted or substituted with at least one R10a to form a C8-C60 polycyclic group (e.g., a carbazole group, etc.) unsubstituted or substituted with at least one R10a (e.g., see 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 selected from groups represented by Formulae CY201 to CY217:




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In Formulae CY201 to CY217, R10b and R10c may each be the same as described herein 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 selected from the groups represented by Formulae CY201 to CY203.


In one or more embodiments, Formula 201 may include at least one selected from the groups represented by Formulae CY201 to CY203 and at least one selected from 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 selected from among Formulae CY201 to CY203, xa2 may be 0, and R202 may be a group represented by one 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 selected from among 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 selected from among Formulae CY201 to CY203, and may include at least one selected from 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 selected from among Formulae CY201 to CY217.


For example, in some embodiments, the hole transport region 120 may include at least one selected from among Compounds HT1 to HT46, 4,4′,4″-[tris(3-methylphenyl)phenylamino] triphenylamine (m-MTDATA), 4,4′,4″-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4′,4″-tris[N-(2-naphthyl)-N-phenylamino]-triphenylamine (2-TNATA), N,N′-di(naphthalene-1-yl)-N,N′-diphenyl-benzidine (NPB(NPD)), β-NPB, N,N′-bis(3-methylphenyl)-N,N′-diphenyl-[1,1′-biphenyl]-4,4′-diamine (TPD), Spiro-TPD, Spiro-NPB, methylated NPB, 4,4′-cyclohexylidene bis[N,N-bis(4-methylphenyl)benzenamine] (TAPC), 4,4′-bis[N,N′-(3-tolyl)amino]-3,3′-dimethylbiphenyl (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), and polyaniline/poly(4-styrenesulfonate) (PANI/PSS), and/or any combination thereof:




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A thickness of the hole transport region 120 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 120 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 120, 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 increase light-emission efficiency by compensating for an optical resonance distance according to the wavelength of light emitted by the emission layer 130, and the electron blocking layer may block or reduce the leakage of electrons from the emission layer 130 to the hole transport region 120. Materials that may be included in the hole transport region 120 may be included in the emission auxiliary layer and the electron blocking layer.


p-Dopant


The hole transport region 120 may further include, in addition to the materials as described above, a charge-generation material for improving conductive properties. The charge-generation material may be uniformly or non-uniformly dispersed in the hole transport region 120 (e.g., in the form of a single layer including (e.g., consisting of) a charge-generation material).


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


For example, the LUMO energy level of the p-dopant may be equal to or less than −3.5 eV.


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


Non-limiting examples of the quinone derivative may include tetracyanoquinodimethane (TCNQ), 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ), and/or the like.


Non-limiting examples of the cyano group-containing compound may include dipyrazino[2,3-f: 2′,3′-h] quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN), a compound represented by Formula 221, and/or the like:




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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 selected from among 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 containing element EL1 and element EL2, element EL1 may be a metal, a metalloid, or any combination thereof, and element EL2 may be a non-metal, a metalloid, or any combination thereof.


Non-limiting examples of the metal may include: an alkali metal (e.g., lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), etc.); an alkaline earth metal (e.g., beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), etc.); a transition metal (e.g., 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), etc.); a post-transition metal (e.g., zinc (Zn), indium (In), tin (Sn), etc.); a lanthanide metal (e.g., 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), etc.); and/or the like.


Non-limiting examples of the metalloid may include silicon (Si), antimony (Sb), tellurium (Te), and/or the like.


Non-limiting examples of the non-metal may include oxygen (O), halogen (e.g., F, Cl, Br, I, etc.), and/or the like.


Non-limiting examples of the compound containing element EL1 and element EL2 may include metal oxide, metal halide (e.g., metal fluoride, metal chloride, metal bromide, metal iodide, etc.), metalloid halide (e.g., metalloid fluoride, metalloid chloride, metalloid bromide, metalloid iodide, etc.), metal telluride, or any combination thereof.


Non-limiting examples of the metal oxide may include tungsten oxide (e.g., WO, W2O3, WO2, WO3, W2O5, etc.), vanadium oxide (e.g., VO, V2O3, VO2, V205, etc.), molybdenum oxide (e.g., MoO, Mo203, MoO2, MoO3, Mo2O5, etc.), rhenium oxide (e.g., ReO3, etc.), and/or the like.


Non-limiting examples of the metal halide may include alkali metal halide, alkaline earth metal halide, transition metal halide, post-transition metal halide, lanthanide metal halide, and/or the like.


Non-limiting examples of the alkali metal halide may include LiF, NaF, KF, RbF, CsF, LiCl, NaCl, KCl, RbCl, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, LiI, NaI, KI, RbI, CsI, and/or the like.


Non-limiting examples of the alkaline earth metal halide may include BeF2, MgF2, CaF2, SrF2, BaF2, BeCl2, MgCl2, CaCl2), SrCl2, BaCl2, BeBr2, MgBr2, CaBr2, SrBr2, BaBr2, BeI2, MgI2, CaI2, SrI2, BaI2, and/or the like.


Non-limiting examples of the transition metal halide may include titanium halide (e.g., TiF4, TiCl4, TiBr4, TiI4, etc.), zirconium halide (e.g., ZrF4, ZrC14, ZrBr4, ZrI4, etc.), hafnium halide (e.g., HfF4, HfCl4, HfBr4, Hfl4, etc.), vanadium halide (e.g., VF3, VCl3, VBr3, VI3, etc.), niobium halide (e.g., NbF3, NbCl3, NbBr3, NbI3, etc.), tantalum halide (e.g., TaF3, TaCl3, TaBr3, TaI3, etc.), chromium halide (e.g., CrF3, CrCl3, CrBr3, CrI3, etc.), molybdenum halide (e.g., MoF3, MoCl3, MoBr3, MoI3, etc.), tungsten halide (e.g., WF3, WCl3, WBr3, WI3, etc.), manganese halide (e.g., MnF2, MnCl2, MnBr2, MnI2, etc.), technetium halide (e.g., TcF2, TcCl2, TcBr2, TcI2, etc.), rhenium halide (e.g., ReF2, ReCl2, ReBr2, ReI2, etc.), ferrous halide (e.g., FeF2, FeCl2, FeBr2, FeI2, etc.), ruthenium halide (e.g., RuF2, RuCl2, RuBr2, RuI2, etc.), osmium halide (e.g., OsF2, OsCl2, OsBr2, OsI2, etc.), cobalt halide (e.g., CoF2, CoCl2, CoBr2, Col2, etc.), rhodium halide (e.g., RhF2, RhCl2, RhBr2, RhI2, etc.), iridium halide (e.g., IrF2, IrCl2, IrBr2, IrI2, etc.), nickel halide (e.g., NiF2, NiCl2, NiBr2, NiI2, etc.), palladium halide (e.g., PdF2, PdCl2, PdBr2, PdI2, etc.), platinum halide (e.g., PtF2, PtCl2, PtBr2, PtI2, etc.), cuprous halide (e.g., CuF, CuCl, CuBr, CuI, etc.), silver halide (e.g., AgF, AgCl, AgBr, AgI, etc.), gold halide (e.g., AuF, AuCl, AuBr, AuI, etc.), and/or the like.


Non-limiting examples of the post-transition metal halide may include zinc halide (e.g., ZnF2, ZnCl2, ZnBr2, ZnI2, etc.), indium halide (e.g., InI3, etc.), tin halide (e.g., SnI2, etc.), and/or the like.


Non-limiting examples of the lanthanide metal halide may include YbF, YbF2, YbF3, SmF3, YbCl, YbCl2, YbCl3, SmCl3, YbBr, YbBr2, YbBr3, SmBr3, YbI, YbI2, YbI3, SmI3, and/or the like.


Non-limiting examples of the metalloid halide may include antimony halide (e.g., SbCl5, etc.) and/or the like.


Non-limiting examples of the metal telluride may include alkali metal telluride (e.g., Li2Te, Na2Te, K2Te, Rb2Te, Cs2Te, etc.), alkaline earth metal telluride (e.g., BeTe, MgTe, CaTe, SrTe, BaTe, etc.), transition metal telluride (e.g., 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, etc.), post-transition metal telluride (e.g., ZnTe, etc.), lanthanide metal telluride (e.g., LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, etc.), and/or the like.


Emission Layer 130

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


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.


In one or more embodiments, 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 above, 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 130 may be patterned into a red emission layer, a green emission layer, and/or a blue emission layer, according to a sub-pixel. In one or more embodiments, the emission layer 130 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 (e.g., combined white light). In one or more embodiments, the emission layer 130 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 (e.g., combined white light).


The emission layer 130 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 130 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 130 may include a quantum dot.


In one or more embodiments, the emission layer 130 may include a delayed fluorescence material. The delayed fluorescence material may act as a host or a dopant in the emission layer 130.


A thickness of the emission layer 130 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 130 is within these ranges, excellent or suitable light-emission characteristics may be obtained without a substantial increase in driving voltage.


Host

The host may include a compound represented by Formula 301:


Formula 301





[Ar301]xb11-[(L301)xb1-R301]xb21.


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-C6 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 may each be the same as described herein with respect to Q1.


For example, in some embodiments, when xb11 in Formula 301 is 2 or more, two or more of Ar301(s) 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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In Formulae 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 the same as described herein,
    • L302 to L304 may each independently be the same as described herein with respect to L301,
    • xb2 to xb4 may each independently be the same as described herein with respect to xb1, and
    • R302 to R305 and R311 to R314 may each be the same as described herein with respect to R301.


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


In one or more embodiments, the host may include at least one 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) and 1,3,5-tri(carbazol-9-yl) benzene (TCP) and/or any combination thereof:




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Phosphorescent Dopant

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.


In some embodiments, the phosphorescent dopant may be electrically neutral.


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




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In Formulae 401 and 402,

    • M may be a transition metal (e.g., 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, when xc1 is 2 or more, two or more of L401(s) may be identical to or different from each other,
    • L402 may be an organic ligand, and xc2 may be 0, 1, 2, 3, or 4, wherein, when xc2 is 2 or more, two or more of L402(s) may be 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 (e.g., a covalent bond or a coordinate bond), O, S, N(Q413), B(Q413), P(Q413), C(Q413)(Q414), or Si(Q413)(Q414),
    • Q411 to Q414 may each be the same 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 the same 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 may 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, when xc1 in Formula 401 is 2 or more, two ring A401(s) in two or more of L401(s) may optionally be linked to each other via T402, which is a linking group, and/or two ring A402(s) may optionally be linked to each other via T403, which is a linking group (see Compounds PD1 to PD4 and PD7). T402 and T403 may each be the same as described herein with respect to T401.


L402 in Formula 401 may be an organic ligand. For example, L402 may include a halogen, a diketone group (e.g., an acetylacetonate group), a carboxylic acid group (e.g., a picolinate group), —C(═O), an isonitrile group, a —CN group, a phosphorus-containing group (e.g., a phosphine group, a phosphite group, etc.), or any combination thereof.


In one or more embodiments, the phosphorescent dopant may include, for example, at least one selected from among Compounds PD1 to PD39, and/or any combination thereof:




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Fluorescent Dopant

In one or more embodiments, the fluorescent dopant may include an amine group-containing compound, a styryl group-containing compound, or any combination thereof.


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




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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, in some embodiments, Ar501 in Formula 501 may be a condensed cyclic group (e.g., an anthracene group, a chrysene group, a pyrene group, etc.) in which three or more monocyclic groups are condensed with each other.


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


For example, in some embodiments, the fluorescent dopant may include at least one selected from among Compounds FD1 to FD37, 4,4′-bis(2,2-diphenylvinyl)-1,1′-biphenyl (DPVBi), and 4,4′-bis[4-(di-p-tolylamino)styryl]biphenyl (DPAVBi), and/or any combination thereof:




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Delayed Fluorescence Material

In one or more embodiments, the emission layer 130 may include a delayed fluorescence material.


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


The delayed fluorescence material included in the emission layer 130 may act as a host or a dopant depending on the type or kind of other materials included in the emission layer 130.


In one or more embodiments, a difference between a triplet energy level (eV) of the delayed fluorescence material and a singlet energy level (eV) of the delayed fluorescence material may be equal to or greater than 0 eV and equal to or less than 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 above-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, in some embodiments, the delayed fluorescence material may include i) a material including at least one electron donor (e.g., a π electron-rich C3-C60 cyclic group, such as a carbazole group, etc.) and at least one electron acceptor (e.g., a sulfoxide group, a cyano group, a π electron-deficient nitrogen-containing C1-C60 cyclic group, etc.), and/or ii) a material including a C8-C60 polycyclic group in which two or more cyclic groups are condensed together while sharing boron (B).


Non-limiting examples of the delayed fluorescence material may include at least one selected from among Compounds DF1 to DF14:




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Quantum Dot

In one or more embodiments, the emission layer 130 may include a quantum dot.


The term “quantum dot” as utilized herein may refer 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 dot 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 quantum dot particle crystal grows, the organic solvent naturally acts as a dispersant coordinated on the surface of the quantum dot particle crystal and controls the growth of the quantum dot particle crystal so that the growth of quantum dot particle crystal 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 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, a Group IV element or compound, or any combination thereof.


Non-limiting examples of the Group II-VI semiconductor compound may include: 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.


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


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


Non-limiting examples of the Group I-III-VI semiconductor compound may include: a ternary compound, such as AgInS, AgInS2, CuInS, CuInS2, CuGaO2, AgGaO2, or AgAlO2.


Non-limiting examples of the Group IV-VI semiconductor compound may include: 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.


The Group IV element or compound may include: a single element, such as Si or Ge; a binary compound, such as SiC or SiGe; 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, a material included in the core and a 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. An 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.


Non-limiting examples of the shell of the quantum dot may include an oxide of metal, metalloid, or non-metal, a semiconductor compound, or any combination thereof. Non-limiting examples of the oxide of metal, metalloid, or non-metal may include: 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; or any combination thereof. Non-limiting examples of the semiconductor compound may include, 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, or 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 an 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 improved. 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 substantially spherical nanoparticle, a pyramidal nanoparticle, a multi-arm nanoparticle, a cubic nanoparticle, a nanotube, a nanowire, a nanofiber, or a nanoplate.


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 an emission layer 130 including the quantum dot. Accordingly, by utilizing quantum dots of different sizes, a light-emitting device 10 that emits light of one or more suitable wavelengths may be implemented. In detail, 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.


Photoactive Layer 135

The opto-electronic device 30 may include the photoactive layer 135 on the hole transport region 120. The photoactive layer 135 may include a first layer 131 adjacent to the hole transport region 120 and a second layer 132 adjacent to the electron transport region 140.


The emission layer 130 may be to emit light to the outside of an electronic apparatus. The light may be reflected by an external object to be incident on the electronic apparatus.


The photoactive layer 135 may generate an electrical signal by absorbing the light incident on the electronic apparatus. Accordingly, the opto-electronic device 30 including the photoactive layer 135 may serve as a photosensor.


Electron Transport Region 140

The electron transport region 140 may be on the emission layer 130 of the light-emitting device 10 and the photoactive layer 135 of the opto-electronic device 30. The electron transport region 140 may have: i) a single-layered structure including (e.g., consisting of) a single layer including (e.g., consisting of) a single material; ii) a single-layered structure including (e.g., consisting of) 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 140 may include a buffer layer, 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 140 may include 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 layers of each structure being sequentially stacked from the emission layer 130 in the stated order.


In one or more embodiments, the electron transport region 140 (e.g., the buffer layer, the hole blocking layer, the electron control layer, or the electron transport layer in the electron transport region 140) may include a metal-free compound including at least one π electron-deficient nitrogen-containing C1-C60 cyclic group.


For example, in some embodiments, the electron transport region 140 may include a compound represented by Formula 601:


Formula 601





[Ar601]xe11-[(L601)xe1-R601]xe21.


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 the same as described herein with respect to Q1,
    • xe21 may be 1, 2, 3, 4, or 5, and
    • at least one selected from among 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, when xe11 in Formula 601 is 2 or more, two or more of Ar601(s) may be linked to each other via a single bond.


In one or more embodiments, Ar601 in Formula 601 may be a substituted or unsubstituted anthracene group.


In one or more embodiments, the electron transport region 140 may include a compound represented by Formula 601-1:




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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 selected from among X614 to X616 may be N,
    • L611 to L613 may each be the same as described herein with respect to L601,
    • xe611 to xe613 may each be the same as described herein with respect to xe1,
    • R611 to R613 may each be the same 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.


In one or more embodiments, the electron transport region 140 may include at least one 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, bis(2-methyl-8-quinolinolato-N1,O8)-(1,1′-biphenyl-4-olato)aluminum (BAlq), 3-(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), and 4-(naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), and/or any combination thereof:




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A thickness of the electron transport region 140 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 140 includes a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, or any combination thereof, a thickness of the buffer layer, the hole blocking layer, or the electron control layer may each independently be in a range of 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 in a range of about 100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. When the thickness of the buffer layer, the hole blocking layer, the electron control layer, the electron transport layer, and/or the electron transport region 140 are within these ranges, satisfactory electron transporting characteristics may be obtained without a substantial increase in driving voltage.


In one or more embodiments, the electron transport region 140 (e.g., the electron transport layer in the electron transport region 140) may further include, in addition to the materials described above, a metal-containing material.


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


For example, in some embodiments, the metal-containing material may include a Li complex. The Li complex may include, for example, Compound ET-D1 (Liq) or ET-D2:




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In one or more embodiments, the electron transport region 140 may include an electron injection layer that facilitates the injection of electrons from the second electrode 150. The electron injection layer may be in direct contact with the second electrode 150.


The electron injection layer may have: i) a single-layered structure including (e.g., consisting of) a single layer including (e.g., consisting of) a single material; ii) a single-layered structure including (e.g., consisting of) 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 (e.g., fluorides, chlorides, bromides, iodides, etc.), 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, LiI, NaI, CsI, or KI, 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), or BaxCa1-xO (wherein x is a real number satisfying the condition of 0<x<1). The rare earth metal-containing compound may include YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3, TbF3, YbI3, ScI3, TbI3, or any combination thereof. In one or more embodiments, the rare earth metal-containing compound may include lanthanide metal telluride. Non-limiting examples of the lanthanide metal telluride may include 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, Lu2Te3, and/or the like.


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, respectively, and ii) a ligand linked 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 (e.g., consist of) 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 above. In one or more embodiments, the electron injection layer may further include an organic material (e.g., a compound represented by Formula 601).


In one or more embodiments, the electron injection layer may include (e.g., consist of) i) an alkali metal-containing compound (e.g., alkali metal halide), or ii) a) an alkali metal-containing compound (e.g., 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, a RbI: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 or 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, for example, about 3 Å to about 90 Å. When the thickness of the electron injection layer is within these ranges, satisfactory electron injection characteristics may be obtained without a substantial increase in driving voltage.


Second Electrode 150

The second electrode 150 may be 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 utilized.


The second electrode 150 may include lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), ytterbium (Yb), silver-ytterbium (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-layered structure or a multi-layered structure including a plurality of layers.


Capping Layer

A first capping layer may be arranged outside the first electrode 110, and/or a second capping layer may be arranged outside the second electrode 150. In some embodiments, the light-emitting device 10 may have a structure in which the first capping layer, the first electrode 110, the emission layer 130, and the second electrode 150 are sequentially stacked in the stated order, a structure in which the first electrode 110, the emission layer 130, the second electrode 150, and the second capping layer are sequentially stacked in the stated order, or a structure in which the first capping layer, the first electrode 110, the emission layer 130, the second electrode 150, and the second capping layer are sequentially stacked in the stated order.


In some embodiments, light generated in the emission layer 130 of the light-emitting device 10 may be extracted toward the outside through the first electrode 110, which is a semi-transmissive electrode or a transmissive electrode, and the first capping layer. In some embodiments, light generated in the emission layer 130 of the light-emitting device 10 may be extracted toward the outside through the second electrode 150, which is a semi-transmissive electrode or a transmissive electrode, and the second capping layer.


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


Each of the first capping layer and the second capping layer may include a material having a refractive index equal to or greater than 1.6 (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 selected from among the first capping layer and the second capping layer may each independently include a carbocyclic compound, a heterocyclic compound, an amine group-containing compound, a porphine derivative, a phthalocyanine derivative, a naphthalocyanine derivative, an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The carbocyclic compound, the heterocyclic compound, and the amine group-containing compound may optionally 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 selected from among the first capping layer and the second capping layer may each independently include an amine group-containing compound.


For example, in some embodiments, at least one selected from among the first capping layer and 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 selected from among the first capping layer and the second capping layer may each independently include at least one selected from among Compounds HT28 to HT33, at least one selected from among Compounds CP1 to CP6, β-NPB, or any combination thereof:




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Film

A film may be, for example, an optical member (or a light control means) (e.g., a color filter, a color conversion member, a capping layer, a light extraction efficiency improvement layer, a selective light-absorbing layer, a polarizing layer, a quantum dot-containing layer, etc.), a light-blocking member (e.g., a light reflection layer, a light-absorbing layer, etc.), a protection member (e.g., an insulating layer, a dielectric material layer, etc.), and/or the like.


Electronic Apparatus

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


The electronic apparatus (e.g., a light-emitting apparatus) may further include, in addition to the light-emitting device 10 and the opto-electronic 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 arranged in at least one direction in which light emitted from the light-emitting device 10 travels. For example, in some embodiments, the light emitted from the light-emitting device 10 may be blue light or white light (e.g., combined white light). Details on the light-emitting device 10 may be the same as described herein. 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 layer may be arranged 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 arranged among the color filter areas, and the color conversion layer may include a plurality of color conversion areas and light-shielding patterns arranged among the color conversion areas.


The color filter areas (or the 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, and the first color light, the second color light, and/or the third color light may have different maximum emission wavelengths. For example, in some embodiments, 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, in one or more embodiments, the color filter areas (or the color conversion areas) may include quantum dots. In some embodiments, the first area may include a red quantum dot to emit red light, the second area may include a green quantum dot to emit green light, and the third area may not include (e.g., may exclude) a quantum dot. Details on the quantum dot may be the same as described herein. The first area, the second area, and/or the third area may each further include a scatterer.


For example, in one or more embodiments, the light-emitting device 10 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 some embodiments, 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.


In one or more embodiments, the electronic apparatus may further include a thin-film transistor, in addition to the light-emitting device 10 as described above. The thin-film transistor may include a source electrode, a drain electrode, and an active layer, and one of the source electrode and the drain electrode may be electrically connected to the first electrode 110 or the second electrode 150 of the light-emitting device 10.


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


The active 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 10. The sealing portion may be arranged between the color filter and/or the color conversion layer and the light-emitting device 10. The sealing portion may allow light from the light-emitting device 10 to be extracted to the outside, and may concurrently (e.g., simultaneously) prevent or reduce ambient air and moisture from penetrating into the light-emitting device 10. 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 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 arranged on the sealing portion, in addition to the color filter and/or the color conversion layer, according to the utilization of the electronic apparatus. Non-limiting 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 utilizing biometric information of a living body (e.g., fingertips, pupils, etc.).


The authentication apparatus may further include, in addition to the light-emitting device 10 as described above, a biometric information collector.


The electronic apparatus may be applied to one or more suitable displays, light sources, lighting, personal computers (e.g., a mobile personal computer), mobile phones, digital cameras, electronic organizers, electronic dictionaries, electronic game machines, medical instruments (e.g., 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 (e.g., meters for a vehicle, an aircraft, and a vessel), projectors, and/or the like.


Electronic Device

The light-emitting device 10 may be included in one or more suitable electronic devices.


For example, the electronic device including the light-emitting device 10 may be one selected from a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor or outdoor lighting and/or signal light, 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 microdisplay, a three-dimensional (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.


The light-emitting device 10 may have excellent or suitable effects in terms of luminescence efficiency and long lifespan, and thus, the electronic device including the light-emitting device 10 may have characteristics, such as high luminance, high resolution, and low power consumption.


Descriptions of FIGS. 3 and 4


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


The electronic apparatus of FIG. 3 may include a substrate 100, a thin-film transistor (TFT), a light-emitting device, and an encapsulation portion 300 that seals the light-emitting device.


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


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


The active 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 active layer 220 from the gate electrode 240 may be arranged on the active layer 220, and the gate electrode 240 may be arranged on the gate insulating film 230.


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


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


The TFT may be electrically connected to a light-emitting device to drive the light-emitting device, and 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. A light-emitting device may be provided on the passivation layer 280. The light-emitting device may include a first electrode 110, an emission layer 130, and a second electrode 150.


The first electrode 110 may be arranged on the passivation layer 280. The passivation layer 280 may not completely cover the drain electrode 270 and may expose a portion of the drain electrode 270, and the first electrode 110 may be connected to the exposed portion of the drain electrode 270.


A pixel defining layer 290 including an insulating material may be arranged on the first electrode 110. The pixel defining layer 290 may expose a portion of the first electrode 110, and the emission layer 130 may be formed in the exposed portion of the first electrode 110. The pixel defining layer 290 may be a polyimide or polyacrylic organic film. In some embodiments, at least some layers of the emission layer 130 may extend beyond the upper portion of the pixel defining layer 290 to be arranged in the form of a common layer.


The second electrode 150 may be arranged on the emission layer 130, and a capping layer 170 may be additionally 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 arranged on the capping layer 170. The encapsulation portion 300 may be arranged on a light-emitting device to protect the light-emitting device from moisture and/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 (e.g., polymethyl methacrylate, polyacrylic acid, etc.), an epoxy-based resin (e.g., aliphatic glycidyl ether (AGE), etc.), or any combination thereof; or a combination of the inorganic film and the organic film.



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


The electronic apparatus of FIG. 4 is substantially 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 FIGS. 3 and/or 4 may be a tandem light-emitting device.


Description of FIG. 5


FIG. 5 is a schematic perspective view of an electronic device 1 including a light-emitting device according to one or more embodiments of the present disclosure. The electronic device 1 may be an apparatus that displays a moving image or a still image, and may include a portable electronic device, 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 device, or an ultra-mobile PC (UMPC), as well as one or more suitable products, such as a television, a laptop, a monitor, a billboard, or an internet of things (IOT) device, or a part thereof. In some embodiments, the electronic device 1 may be a wearable device, such as a smart watch, a watch phone, a glasses-type or kind display, or a head mounted display (HMD), or a part thereof. However, embodiments of the present disclosure are not limited thereto. For example, the electronic device 1 may be an instrument panel of a vehicle, a center information display (CID) arranged on a center fascia or a dashboard of a vehicle, a room mirror display that replaces a side mirror of a vehicle, an entertainment display for a rear seat of a vehicle or a display arranged on a rear surface of a front seat, a head up display (HUD) installed at a front of a vehicle or projected on a front window glass, or a computer generated hologram augmented reality head up display (CGH AR HUD). For convenience of description, FIG. 5 shows an embodiment in which the electronic device 1 is a smart phone.


The electronic device 1 may include a display area DA and a non-display area NDA outside the display area DA. A display apparatus of the electronic device 1 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 may be an area in which an image is not displayed, and may entirely surround the display area DA. A driver for providing electrical signals or power to display elements arranged in the display area DA may be arranged in the non-display area NDA. A pad, which is an area to which an electronic element or a printed circuit board may be electrically connected, may be arranged in the non-display area NDA.


The electronic device 1 may have different lengths in the x-axis direction and in the y-axis direction and a thickness in a z-axis direction crossing the x-axis direction and the y-axis direction. For example, as shown in FIG. 5, the length in the x-axis direction may be shorter than the length in the y-axis direction. In one or more embodiments, the length in the x-axis direction may be substantially 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 schematic view of the exterior of a vehicle 1000 as an electronic device including a light-emitting device according to one or more embodiments of the present disclosure. FIGS. 7A to 7C are schematic views of the interior of the vehicle 1000 according to one or more embodiments of the present disclosure.


Referring to FIGS. 6, 7A, 7B, and 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. The vehicle 1000 may include a vehicle traveling on a road or a track, a vessel moving over the sea or a river, or an airplane flying in the sky by utilizing the action of air.


In one or more embodiments, the vehicle 1000 may travel on a road or a track. The vehicle 1000 may move in a certain direction according to 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 motorbike, a bicycle, or 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 the remaining parts except for the body. The exterior of the body may include a front panel, a bonnet, a roof panel, a rear panel, a trunk, and a pillar provided at a boundary between doors. The chassis of the vehicle 1000 may include a power generating apparatus, a power transmitting apparatus, a driving apparatus, a steering apparatus, a braking apparatus, a suspension apparatus, a transmission apparatus, a fuel apparatus, 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 a side surface 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 apart from each other in the x-direction or the direction opposite to the x-direction. For example, the first side window glass 1110 and the second side window glass 1120 may be spaced apart from each other in the x direction or the direction opposite to the x-direction. In other words, an imaginary straight line L connecting the side window glasses 1100 to each other may extend in the x direction or the direction opposite to the x-direction. For example, the 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 direction opposite to 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 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 body. In one or more embodiments, a plurality of side mirrors 1300 may be provided. One of the plurality of side mirrors 1300 may be arranged outside the first side window glass 1110. Another 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, a direction change indicator light, a high beam indicator light, a warning light, a seat belt warning light, an odometer, a hodometer, an automatic transmission selection lever indicator light, a door open warning light, an engine oil warning light, 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 apparatus, an air conditioning apparatus, and a heater of a seat are arranged. The center fascia 1500 may be arranged on one side of the cluster 1400.


The passenger seat dashboard 1600 may be spaced apart from the cluster 1400 with the center fascia 1500 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 some embodiments, the display apparatus 2 may be arranged between the side window glasses 1100 facing each other. The display apparatus 2 may be arranged on at least one selected from among 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 light-emitting device according to the present disclosure will be described as an example of the display apparatus 2. However, one or more suitable types (kinds) of display apparatuses as described above may be utilized in embodiments of the present disclosure.


Referring to FIG. 7A, the display apparatus 2 may be arranged on the center fascia 1500. In one embodiment, the display apparatus 2 may display navigation information. In another embodiment, 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. The cluster 1400 may display driving information and/or the like through the display apparatus 2. For example, in some embodiments, the cluster 1400 may be digitally implemented. 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 digital signals.


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 some 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 that is different from information displayed on the cluster 1400 and/or information displayed on the center fascia 1500.


Manufacturing Method

Respective layers included in the hole transport region 120, the emission layer 130, the first and second layers 131 and 132 included in the photoactive layer 135, and respective layers included in the electron transport region 140 may be formed in a certain region by utilizing one or more suitable methods selected from vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) method, ink-jet printing, laser-printing, and laser-induced thermal imaging (LITI).


When respective layers included in the hole transport region 120, the emission layer 130, the first and second layers 131 and 132 included in the photoactive layer 135, and respective layers included in the electron transport region 140 are formed by vacuum deposition, the vacuum deposition may be performed at a deposition temperature of about 100° C. to about 500° C., a vacuum degree of about 108 torr to about 10−3 torr, and a deposition speed of about 0.01 Å/sec to about 100 Å/sec, depending on a material to be included in a layer to be formed and the structure of a layer to be formed. Because the organic compound according to one or more embodiments of the present disclosure, in which a first moiety represented by Formula 2 and a second moiety represented by Formula 3 are bonded together, has excellent or suitable heat resistance, when the second layer 132 included in the photoactive layer 135 is formed by vacuum deposition by utilizing the organic compound, the second layer 132 may be easily formed without defects.


Definitions of Terms

The term “C3-C60 carbocyclic group” as utilized herein refers to a cyclic group consisting of carbon only as a ring-forming atom and having 3 to 60 carbon atoms, and the term “C1-C60 heterocyclic group” as utilized 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 consisting of one ring or a polycyclic group in which two or more rings are condensed with each other. For example, the C1-C60 heterocyclic group may have 3 to 61 ring-forming atoms.


The “cyclic group” as utilized 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 utilized herein refers to a cyclic group that has 3 to 60 carbon atoms and does not include *—N═*′ as a ring-forming moiety, and the term “π electron-deficient nitrogen-containing C1-C60 cyclic group” as utilized herein refers to a heterocyclic group that has 1 to 60 carbon atoms and includes *—N═*′ as a ring-forming moiety.


In one or more embodiments,

    • the C3-C60 carbocyclic group may be i) a group T1 or ii) a condensed cyclic group in which two or more groups T1 are condensed with each other (e.g., 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) a 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 (e.g., 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, etc.),
    • the π electron-rich C3-C60 cyclic group may be i) a group T1, ii) a condensed cyclic group in which two or more groups T1 are condensed with each other, iii) a 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 (e.g., 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, etc.), and
    • the π electron-deficient nitrogen-containing C1-C60 cyclic group may be i) a 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 each other (e.g., 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, etc.),
    • wherein the 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 a 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,
    • the 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,
    • the group T3 may be a furan group, a thiophene group, a 1 H-pyrrole group, a silole group, or a borole group, and
    • the 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 “cyclic group,” “C3-C60 carbocyclic group,” “C1-C60 heterocyclic group,” “π electron-rich C3-C60 cyclic group,” and “π electron-deficient nitrogen-containing C1-C60 cyclic group” as utilized herein refer to a group condensed with any cyclic group, a monovalent group, or a polyvalent group (e.g., a divalent group, a trivalent group, a tetravalent group, etc.), depending on the structure of a formula in connection with which the terms are utilized. 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.”


Non-limiting examples of the monovalent C3-C60 carbocyclic group and the monovalent C1-C60 heterocyclic group may include 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, and non-limiting examples of the divalent C3-C60 carbocyclic group and the divalent C1-C60 heterocyclic group may include 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 divalent non-aromatic condensed heteropolycyclic group.


The term “C1-C60 alkyl group” as utilized herein refers to a linear or branched aliphatic saturated hydrocarbon monovalent group that has 1 to 60 carbon atoms, and non-limiting examples thereof may include 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, a tert-decyl group, and/or the like. The term “C1-C60 alkylene group” as utilized herein refers to a divalent group having the same structure as the C1-C60 alkyl group.


The term “C2-C60 alkenyl group” as utilized 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 non-limiting examples thereof may include an ethenyl group, a propenyl group, a butenyl group, and/or the like. The term “C2-C60 alkenylene group” as utilized herein refers to a divalent group having the same structure as the C2-C60 alkenyl group.


The term “C2-C60 alkynyl group” as utilized 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 non-limiting examples thereof may include an ethynyl group, a propynyl group, and/or the like. The term “C2-C60 alkynylene group” as utilized herein refers to a divalent group having the same structure as the C2-C60 alkynyl group.


The term “C1-C60 alkoxy group” as utilized herein refers to a monovalent group represented by -OA101 (wherein A101 is the C1-C60 alkyl group), and non-limiting examples thereof may include a methoxy group, an ethoxy group, an isopropyloxy group, and/or the like.


The term “C3-C10 cycloalkyl group” as utilized herein refers to a monovalent saturated hydrocarbon cyclic group having 3 to 10 carbon atoms, and non-limiting examples thereof may include 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 a bicyclo[2.2.1]heptyl group), a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.2]octyl group, and/or the like. The term “C3-C10 cycloalkylene group” as utilized herein refers to a divalent group having the same structure as the C3-C10 cycloalkyl group.


The term “C1-C10 heterocycloalkyl group” as utilized herein refers to a monovalent cyclic group that further includes, in addition to a carbon atom, at least one heteroatom as a ring-forming atom and has 1 to 10 carbon atoms, and non-limiting examples thereof may include a 1,2,3,4-oxatriazolidinyl group, a tetrahydrofuranyl group, a tetrahydrothiophenyl group, and/or the like. The term “C1-C10 heterocycloalkylene group” as utilized herein refers to a divalent group having the same structure as the C1-C10 heterocycloalkyl group.


The term “C3-C10 cycloalkenyl group” as utilized 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 non-limiting examples thereof may include a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, and/or the like. The term “C3-C10 cycloalkenylene group” as utilized herein refers to a divalent group having the same structure as the C3-C10 cycloalkenyl group.


The term “C1-C10 heterocycloalkenyl group” as utilized 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 double bond in the cyclic structure thereof. Non-limiting examples of the C1-C60 heterocycloalkenyl group may include a 4,5-dihydro-1,2,3,4-oxatriazolyl group, a 2,3-dihydrofuranyl group, a 2,3-dihydrothiophenyl group, and/or the like. The term “C1-C10 heterocycloalkenylene group” as utilized herein refers to a divalent group having the same structure as the C1-C10 heterocycloalkenyl group.


The term “C6-C60 aryl group” as utilized herein refers to a monovalent group having a carbocyclic aromatic system of 6 to 60 carbon atoms, and the term “C6-C60 arylene group” as utilized herein refers to a divalent group having a carbocyclic aromatic system of 6 to 60 carbon atoms. Non-limiting examples of the C6-C60 aryl group may include 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, an ovalenyl group, and/or the like. When the C6-C60 aryl group and the C6-C60 arylene group each include two or more rings, the two or more rings may be condensed with each other.


The term “C1-C60 heteroaryl group” as utilized 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, and the term “C1-C60 heteroarylene group” as utilized 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. Non-limiting examples of the C1-C60 heteroaryl group may include 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, a naphthyridinyl group, and/or the like. When the C1-C60 heteroaryl group and the C1-C60 heteroarylene group each include two or more rings, the two or more rings may be condensed with each other.


The term “monovalent non-aromatic condensed polycyclic group” as utilized herein refers to a monovalent group having two or more rings condensed with each other, only carbon atoms (e.g., 8 to 60 carbon atoms) as ring-forming atoms, and no aromaticity in its entire molecular structure as a whole. Non-limiting examples of the monovalent non-aromatic condensed polycyclic group may include an indenyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, an indenophenanthrenyl group, an indenoanthracenyl group, and/or the like. The term “divalent non-aromatic condensed polycyclic group” as utilized herein refers to a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.


The term “monovalent non-aromatic condensed heteropolycyclic group” as utilized herein refers to a monovalent group having two or more rings condensed with each other, at least one heteroatom other than carbon atoms (e.g., 1 to 60 carbon atoms), as a ring-forming atom, and no aromaticity in its entire molecular structure as a whole. Non-limiting examples of the monovalent non-aromatic condensed heteropolycyclic group may include a pyrrolyl group, a thiophenyl group, a furanyl group, an indolyl group, a benzoindolyl group, a naphtho indolyl 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 indenocarbazolyl 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 benzonaphthosilolyl group, a benzofurodibenzofuranyl group, a benzofurodibenzothiophenyl group, a benzothienodibenzothiophenyl group, and/or the like. The term “divalent non-aromatic condensed heteropolycyclic group” as utilized herein refers to a divalent group having the same structure as the monovalent non-aromatic condensed heteropolycyclic group.


The term “C6-C60 aryloxy group” as utilized herein refers to —OA102 (wherein A102 is the C6-C60 aryl group), and the term “C6-C60 arylthio group” as utilized herein refers to —SA103 (wherein A103 is the C6-C60 aryl group).


The term “C7-C0 arylalkyl group” as utilized herein refers to -A104A105 (wherein A104 is a C1-C54 alkylene group, and A105 is a C6-C59 aryl group), and the term “C2-C60 heteroarylalkyl group” as utilized herein refers to -A106A107 (wherein A106 is a C1-C59 alkylene group, and A107 is a C1-C59 heteroaryl group).


The term “R10a” as utilized herein refers to:

    • 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 arylalkyl group, a C2-C60 heteroarylalkyl 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 arylalkyl group, or a C2-C60 heteroarylalkyl 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 arylalkyl group, a C2-C60 heteroarylalkyl 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 as utilized 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 arylalkyl group; or a C2-C60 heteroarylalkyl group.


The term “heteroatom” as utilized herein refers to any atom other than a carbon atom. Non-limiting examples of the heteroatom may include O, S, N, P, Si, B, Ge, Se, or any combination thereof.


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


The term “Ph” as utilized herein refers to a phenyl group, the term “Me” as utilized herein refers to a methyl group, the term “Et” as utilized herein refers to an ethyl group, the term “tert-Bu” or “But” as utilized herein refers to a tert-butyl group, and the term “OMe” as utilized herein refers to a methoxy group.


The term “biphenyl group” as utilized herein refers to “a phenyl group substituted with a phenyl group.” In other words, the “biphenyl group” is a substituted phenyl group having a C6-C60 aryl group as a substituent.


The term “terphenyl group” as utilized herein refers to “a phenyl group substituted with a biphenyl group.” In other words, 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 utilized herein, unless defined otherwise, each refer to a binding site to a neighboring atom in a corresponding formula or moiety.


The x-axis, y-axis, and z-axis as utilized herein 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.


Hereinafter, compounds according to embodiments and light-emitting devices according to embodiments of the present disclosure will be described in more detail with reference to Synthesis Examples and Examples. The wording “B was utilized instead of A” utilized in describing Synthesis Examples may refer to that an identical molar equivalent of B was utilized in place of an identical molar equivalent of A.


Synthesis Example 1 (Synthesis of Compound 1)



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Synthesis of Intermediate a

In an argon atmosphere, 4H-cyclopenta[2,1-b:3,4-b′]dithiophene-4-one (4.0 g, 21 mmol) was dissolved in 50 mL of DMF, N-bromosuccinimide (NBS) (4.6 g, 21 mmol) was added thereto, and the resultant mixture was stirred at room temperature for 12 hours. After completion of the reaction, the solvent was removed therefrom under a reduced pressure, and the resultant product was separated and purified by column chromatography utilizing ethyl acetate and hexane to thereby obtain Intermediate a (red solid, 7.2 g, 96%).


By measuring the molecular weight of the obtained compound through electrospray ionization-liquid chromatography mass spectrometry (ESI-LCMS), the obtained compound was identified as intermediate a. (ESI-LCMS: [M]+: C9H2Br2OS2. 347.79.)




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Synthesis of Intermediate 1-b

In an argon atmosphere, 2,2′-(5,5-difluoro-4H-cyclopenta[b]thiophene-4,6(5H)-diylidene)dimalononitrile (0.3 g, 1.0 mmol) was dissolved in 20 mL of THF and cooled to a temperature of −78° C. n-BuLi (2.7 mL, 1.6 M in hexanes, 4 mmol) was added dropwise thereto for 10 minutes, and the resultant mixture was stirred at the same temperature for 1 hour. Bu3SnCl (0.4 g, 1.2 mmol) was added dropwise thereto for 10 minutes, and the resultant mixture was stirred at room temperature for 17 hours. After completion of the reaction, the solvent was removed therefrom under a reduced pressure, and the resultant product was separated and purified by column chromatography utilizing ethyl acetate and hexane to thereby obtain Intermediate 1-b (0.5 g, 80%).


By measuring the molecular weight of the obtained compound through ESI-LCMS, the obtained compound was identified as Intermediate 1-b. (ESI-LCMS: [M]+: C25H28F2N4SSn. 574.10.)


Synthesis of Intermediate 1-c

In an argon atmosphere, Intermediate a (0.2 g, 0.6 mmol), Intermediate 1-b (0.5 g, 0.8 mmol), and Pd(PPh3)4(10 mg) were dissolved in 30 mL of dry toluene, and the resultant solution was heated and stirred at a temperature of 80° C. for 12 hours. After cooling, an extraction process was performed thereon by utilizing water (500 mL) and ethyl acetate (300 mL) to collect an organic layer, and the resultant solution was dried utilizing anhydrous MgSO4 and filtered. The filtered solution was subjected to a reduced pressure to remove the solvent therefrom, and the resultant solid was separated and purified by column chromatography utilizing CH2Cl2 and hexane to thereby obtain Intermediate 1-c (0.3 g, 0.4 mmol, 75%).


By measuring the molecular weight of the obtained compound through ESI-LCMS, the obtained compound was identified as Intermediate 1-c. (ESI-LCMS: [M]+: C35H4F4N8OS4. 755.93.)


Synthesis of Compound 1

In an argon atmosphere, Intermediate 1-c (0.3 g, 0.4 mmol) was dissolved in 5 mL of chloroform (CHCl3), malononitrile (0.03 g, 0.5 mmol), 5 mL of a methanol (CH3OH) solution, and 1 mL of Et3N were added thereto, and the resultant solution was stirred at room temperature for 35 minutes and concentrated under a reduced pressure. The resultant solid was separated and purified by column chromatography utilizing CH2Cl2 and hexane to thereby obtain Compound 1 (0.2 g, 0.3 mmol, 60%).


By measuring the molecular weight of the obtained compound through ESI-LCMS, the obtained compound was identified as Compound 1. (ESI-LCMS: [M]+: C38H4F4N10S4. 803.94.)


Synthesis Example 2 (Synthesis of Compound 8)



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Synthesis of Intermediate 8-b

In an argon atmosphere, thiophene-2-carbonitrile (0.1 g, 1.0 mmol) was dissolved in 20 mL of THF and cooled to a temperature of −78° C. n-BuLi (2.7 mL, 1.6 M in hexanes, 4 mmol) was added dropwise thereto for 10 minutes, and the resultant mixture was stirred at the same temperature for 1 hour. Bu3SnCl (0.4 g, 1.2 mmol) was added dropwise thereto for 10 minutes, and the resultant mixture was stirred at room temperature for 17 hours. After completion of the reaction, the solvent was removed therefrom under a reduced pressure, and the resultant product was separated and purified by column chromatography utilizing ethyl acetate and hexane to thereby obtain Intermediate 8-b (0.3 g, 0.8 mmol, 80%).


By measuring the molecular weight of the obtained compound through ESI-LCMS, the obtained compound was identified as Intermediate 8-b. (ESI-LCMS: [M]+: C17H29NSSn. 399.10.)


Synthesis of Intermediate 8-c

In an argon atmosphere, Intermediate a (0.2 g, 0.6 mmol), Intermediate 8-b (0.3 g, 0.8 mmol), and Pd(PPh3)4(10 mg) were dissolved in 30 mL of dry toluene, and the resultant solution was heated and stirred at a temperature of 80° C. for 12 hours. After cooling, an extraction process was performed thereon by utilizing water (500 mL) and ethyl acetate (300 mL) to collect an organic layer, and the resultant solution was dried utilizing anhydrous MgSO4 and filtered. The filtered solution was subjected to a reduced pressure to remove the solvent therefrom, and the resultant solid was separated and purified by column chromatography utilizing CH2Cl2 and hexane to thereby obtain Intermediate 8-c (0.2 g, 0.4 mmol, 75%).


By measuring the molecular weight of the obtained compound through ESI-LCMS, the obtained compound was identified as Intermediate 8-c. (ESI-LCMS: [M]+: C19H6N2OS4. 405.94.)


Synthesis of Compound 8

In an argon atmosphere, Intermediate 8-c (0.2 g, 0.4 mmol) was dissolved in 5 mL of chloroform (CHCl3), malononitrile (0.03 g, 0.5 mmol), 5 mL of a methanol (CH3OH) solution, and 1 mL of Et3N were added thereto, and the resultant solution was stirred at room temperature for 35 minutes and concentrated under a reduced pressure. The resultant solid was separated and purified by column chromatography utilizing CH2Cl2 and hexane to thereby obtain Compound 8 (0.13 g, 0.3 mmol, 60%).


By measuring the molecular weight of the obtained compound through ESI-LCMS, the obtained compound was identified as Compound 8. (ESI-LCMS: [M]+: C22H6N4S4. 453.95.)


Synthesis Example 3 (Synthesis of Compound 12)



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Synthesis of Intermediate 12-a

In an argon atmosphere, 4H-cyclopenta[2,1-b:3,4-b′]bis(selenophene)-4-one (6.0 g, 21 mmol) was dissolved in 50 mL of DMF, NBS (4.6 g, 21 mmol) was added thereto, and the resultant mixture was stirred at room temperature for 12 hours. After completion of the reaction, the solvent was removed therefrom under a reduced pressure, and the resultant product was separated and purified by column chromatography utilizing ethyl acetate and hexane to thereby obtain Intermediate 12-a (red solid, 9.2 g, 96%).


By measuring the molecular weight of the obtained compound through ESI-LCMS, the obtained compound was identified as Intermediate 12-a. (ESI-LCMS: [M]+: C9H2Br2OSe2. 443.68.)




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Synthesis of Intermediate 12-b

The synthesis of Intermediate 12-b was carried out in substantially the same manner as in the synthesis of Intermediate 8-b.


Synthesis of Intermediate 12-c

In an argon atmosphere, Intermediate 12-a (0.3 g, 0.6 mmol), Intermediate 12-b (0.3 g, 0.8 mmol), and Pd(PPh3)4(10 mg) were dissolved in 30 mL of dry toluene, and the resultant solution was heated and stirred at a temperature of 80° C. for 12 hours. After cooling, an extraction process was performed thereon by utilizing water (500 mL) and ethyl acetate (300 mL) to collect an organic layer, and the resultant solution was dried utilizing anhydrous MgSO4 and filtered. The filtered solution was subjected to a reduced pressure to remove the solvent therefrom, and the resultant solid was separated and purified by column chromatography utilizing CH2Cl2 and hexane to thereby obtain Intermediate 12-c (0.2 g, 0.4 mmol, 74%).


By measuring the molecular weight of the obtained compound through ESI-LCMS, the obtained compound was identified as Intermediate 12-c. (ESI-LCMS: [M]*: C19H6N2OS2Se2. 501.83.)


Synthesis of Compound 12

In an argon atmosphere, Intermediate 12-c (0.2 g, 0.4 mmol) was dissolved in 5 mL of chloroform (CHCl3), malononitrile (0.03 g, 0.5 mmol), 5 mL of a methanol (CH3OH) solution, and 1 mL of Et3N were added thereto, and the resultant solution was stirred at room temperature for 35 minutes and concentrated under a reduced pressure. The resultant solid was separated and purified by column chromatography utilizing CH2Cl2 and hexane to thereby obtain Compound 12 (0.15 g, 0.3 mmol, 59%).


By measuring the molecular weight of the obtained compound through ESI-LCMS, the obtained compound was identified as Compound 12. (ESI-LCMS: [M]+: C22H6N4S2Se2. 549.84.)


Synthesis Example 4 (Synthesis of Compound 14)



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Synthesis of Intermediate 14-b

In an argon atmosphere, benzo[c]thiophene-5,6-dicarbonitrile (0.2 g, 1.0 mmol) was dissolved in 20 mL of THF and cooled to a temperature of −78° C. n-BuLi (2.7 mL, 1.6 M in hexanes, 4 mmol) was added dropwise thereto for 10 minutes, and the resultant mixture was stirred at the same temperature for 1 hour. Bu3SnCl (0.4 g, 1.2 mmol) was added dropwise thereto for 10 minutes, and the resultant mixture was stirred at room temperature for 17 hours. After completion of the reaction, the solvent was removed therefrom under a reduced pressure, and the resultant product was separated and purified by column chromatography utilizing ethyl acetate and hexane to thereby obtain Intermediate 14-b (0.4 g, 0.8 mmol, 80%).


By measuring the molecular weight of the obtained compound through ESI-LCMS, the obtained compound was identified as Intermediate 14-b. (ESI-LCMS: [M]+: C22H30N2SSn. 474.12.)


Synthesis of Intermediate 14-c

In an argon atmosphere, Intermediate a (0.2 g, 0.6 mmol), Intermediate 14-b (0.4 g, 0.8 mmol), and Pd(PPh3)4(10 mg) were dissolved in 30 mL of dry toluene, and the resultant solution was heated and stirred at a temperature of 80° C. for 12 hours. After cooling, an extraction process was performed thereon by utilizing water (500 mL) and ethyl acetate (300 mL) to collect an organic layer, and the resultant solution was dried utilizing anhydrous MgSO4 and filtered. The filtered solution was subjected to a reduced pressure to remove the solvent therefrom, and the resultant solid was separated and purified by column chromatography utilizing CH2Cl2 and hexane to thereby obtain Intermediate 14-c (0.2 g, 0.4 mmol, 72%).


By measuring the molecular weight of the obtained compound through ESI-LCMS, the obtained compound was identified as Intermediate 14-c. (ESI-LCMS: [M]+: C29H8N4OS4. 555.96.)


Synthesis of Compound 14

In an argon atmosphere, Intermediate 14-c (0.2 g, 0.4 mmol) was dissolved in 5 mL of chloroform (CHCl3), malononitrile (0.03 g, 0.5 mmol), 5 mL of a methanol (CH3OH) solution, and 1 mL of Et3N were added thereto, and the resultant solution was stirred at room temperature for 35 minutes and concentrated under a reduced pressure. The resultant solid was separated and purified by column chromatography utilizing CH2Cl2 and hexane to thereby obtain Compound 14 (0.18 g, 0.3 mmol, 62%).


By measuring the molecular weight of the obtained compound through ESI-LCMS, the obtained compound was identified as Compound 14. (ESI-LCMS: [M]+: C32H8N6S4. 603.97.)


Evaluation Example 1

To evaluate the characteristics of a compound utilized in a second layer in each of Comparative Examples 1 and 2 and Examples 1 to 4, the HOMO energy level, LUMO energy level, and electron affinity (EA) thereof were measured, and the results are shown in Table 1. In evaluating the characteristics, quantum simulation was performed at the B3LYP/6-311 G** level based on the time-dependent density functional theory (TD-DFT) methodology by utilizing the Gaussian program, to measure energy levels in a structurally optimized state and an excited state (HOMO/LUMO energy levels) and a difference between a structurally optimized energy level in a neutral state and a structurally optimized energy level in an anion state (EA).














TABLE 1








HOMO
LUMO
EA



Acceptor
[eV]
[eV]
[eV]






















Example 1
Compound 1
−6.46
−4.11
3.31



Example 2
Compound 8
−6.53
−5.09
4.12



Example 3
Compound 12
−6.67
−5.13
4.17



Example 4
Compound 14
−6.23
−4.21
2.93



Comparative
Fullerene
−6.40
−3.66
2.52



Example 1



Comparative
Compound A
−5.89
−3.70
2.85



Example 2












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Example 1

As an anode, a glass substrate with a 15 Ω/cm2 (1,200 Å) ITO formed thereon (available from Corning Co., Ltd) was cut to a size of 50 mm×50 mm×0.7 mm, sonicated in isopropyl alcohol and pure water for 5 minutes each, cleaned by irradiation of ultraviolet rays and exposure of ozone thereto for 30 minutes, and 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, referred to as NPB) was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 1,250 Å.


Boron subphthalocyanine chloride (hereinafter, referred to as SubPC) was vacuum-deposited on the hole transport layer to form a first layer included in a photoactive layer, the first layer having a thickness of 200 Å.


Compound 1 was vacuum-deposited on the first layer to form a second layer included in the photoactive layer, the second layer having a thickness of 250 Å.


BAlq was vacuum-deposited on the second layer to form a hole blocking layer having a thickness of 50 Å, and Alq3 and ET1 were vacuum-deposited on the hole blocking layer to form an electron transport layer having a thickness of 300 Å. LiF and Liq were vacuum-deposited on the electron transport layer to form an electron injection layer having a thickness of 10 Å. Al and AgMg were sequentially vacuum-deposited on the electron injection layer to form cathodes having thicknesses of 3,000 Å and 100 Å, respectively, thereby completing the manufacture of an opto-electronic device:




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Examples 2 to 4 and Comparative Examples 1 and 2

Compared to Example 1, opto-electronic devices were manufactured in substantially the same manner as in Example 1, except that a second layer including an acceptor compound shown in Table 2, instead of Compound 1, was formed on a first layer.


Evaluation Example 2

To evaluate the characteristics of the opto-electronic devices manufactured in Examples 1 to 4 and Comparative Examples 1 and 2, the external quantum efficiency (EQE) and dark current density (Jdark) thereof were measured, and the results are shown in Table 2.


In measuring the external quantum efficiency (EQE), a current value generated when a manufactured opto-electronic device was irradiated with light (530 nm) by utilizing an external quantum efficiency meter (K3100, McScience, Korea) was measured by utilizing an ammeter (Keithley, Tektronix, USA), and the measured current value was calculated as an external quantum efficiency (EQE) value.


The dark current density (Jdark) was measured by utilizing an ammeter (Keithley, Tektronix, USA) after applying a voltage to an anode at a dark current density with a reverse bias of −3 V by utilizing an electro-optical characteristics evaluation equipment (K3100, McScience, Korea).














TABLE 2









EQE
Jdark



Donor
Acceptor
[%]
[mA/cm2]




















Example 1
SubPc
Compound 1
28
2.7 × 10−6


Example 2
SubPc
Compound 8
32
4.2 × 10−6


Example 3
SubPc
Compound 12
37
4.8 × 10−6


Example 4
SubPc
Compound 14
25
3.7 × 10−6


Comparative
SubPc
Fullerene
20
3.5 × 10−6


Example 1


Comparative
SubPc
Compound A
22
4.3 × 10−6


Example 2









Referring to Tables 1 and 2, the opto-electronic devices according to Examples 1 to 4 had a relatively low LUMO energy level, and also had improved photoelectric efficiency by including an organic compound of the present disclosure having excellent or suitable electron affinity, as compared with the opto-electronic devices according to Comparative Examples 1 and 2 that did not include the organic compound of the present disclosure.


According to the one or more embodiments, an organic compound represented by Formula 1 may have a low LUMO energy level, and may also have electron affinity characteristics by including an EWG. The organic compound may have excellent or suitable stability in a negatively charged state, thereby having an improved degree of separation between electrons and holes. Accordingly, an opto-electronic device including the organic compound may have improved energy efficiency. An electronic apparatus including the opto-electronic device and an electronic device utilizing the electronic apparatus may have improved quality.


In the present disclosure, singular expressions may include plural expressions unless the context clearly indicates otherwise. It will be further understood that the terms “comprise,” “include,” or “have” when utilized in the present disclosure, specify the presence of stated features, integers, steps, operations, elements, and/or components, but do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, components, and/or groups thereof. The “/” utilized below may be interpreted as “and” or as “or” depending on the situation.


Throughout the present disclosure, when a component such as a layer, a film, a region, or a plate is mentioned to be placed “on” another component, it will be understood that it may be directly on the another component or that another component may be interposed therebetween. In some embodiments, “directly on” may refer to that there are no additional layers, films, regions, plates, etc., between a layer, a film, a region, a plate, etc. and the other part. For example, “directly on” may refer to two layers or two members are disposed without utilizing an additional member such as an adhesive member therebetween.


In the present disclosure, although the terms “first,” “second,” etc., may be utilized herein to describe one or more elements, components, regions, and/or layers, these elements, components, regions, and/or layers should not be limited by these terms. These terms are only utilized to distinguish one component from another component.


As utilized herein, the singular forms “a,” “an,” and “the” are intended to include the plural forms as well, unless the context clearly indicates otherwise. Further, the use of “may” when describing embodiments of the present disclosure refers to “one or more embodiments of the present disclosure”.


In the present disclosure, when particles are spherical, “diameter” indicates a particle diameter or an average particle diameter, and when the particles are non-spherical, the “diameter” indicates a major axis length or an average major axis length. The diameter (or size) of the particles may be measured utilizing a scanning electron microscope or a particle size analyzer. As the particle size analyzer, for example, HORIBA, LA-950 laser particle size analyzer, may be utilized. When the size of the particles is measured utilizing a particle size analyzer, the average particle diameter (or size) is referred to as D50. D50 refers to the average diameter (or size) of particles whose cumulative volume corresponds to 50 vol % in the particle size distribution (e.g., cumulative distribution), and refers to the value of the particle size corresponding to 50% from the smallest particle when the total number of particles is 100% in the distribution curve accumulated in the order of the smallest particle size to the largest particle size.


As utilized herein, the terms “substantially,” “about,” or similar terms are used as terms of approximation 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. “About” as used herein, is inclusive of the stated value and means within an acceptable range of deviation for the particular value as determined by one of ordinary skill in the art, considering the measurement in question and the error associated with measurement of the particular quantity (i.e., the limitations of the measurement system). For example, “about” may mean within one or more standard deviations, or within ±30%, 20%, 10%, 5% of the stated value.


Any numerical range recited herein is intended to include all sub-ranges of the same numerical precision subsumed within the recited range. For example, a range of “1.0 to 10.0” is intended to include all subranges between (and including) the recited minimum value of 1.0 and the recited maximum value of 10.0, that is, 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. Any maximum numerical limitation recited herein is intended to include all lower numerical limitations subsumed therein and any minimum numerical limitation recited in this specification is intended to include all higher numerical limitations subsumed therein. Accordingly, Applicant reserves the right to amend this specification, including the claims, to expressly recite any sub-range subsumed within the ranges expressly recited herein.


The opto-electronic device, the light-emitting device, the display apparatus, the electronic apparatus, the electronic device, 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 device may be formed on one integrated circuit (IC) chip or on separate IC chips. Further, the various components of the device 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 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.


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 other 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 claims and equivalents thereof.

Claims
  • 1. An opto-electronic device comprising: a first electrode;a second electrode facing the first electrode;a photoactive layer between the first electrode and the second electrode; andan organic compound represented by Formula 1:
  • 2. The opto-electronic device of claim 1, wherein the opto-electronic device further comprises a hole transport region between the first electrode and the photoactive layer and an electron transport region between the photoactive layer and the second electrode, and the photoactive layer comprises the organic compound.
  • 3. The opto-electronic device of claim 2, wherein the photoactive layer comprises a first layer adjacent to the hole transport region and a second layer adjacent to the electron transport region, and the second layer comprises the organic compound.
  • 4. The opto-electronic device of claim 3, wherein the first layer comprises a donor compound, and the second layer comprises the organic compound which is an acceptor compound, and a lowest unoccupied molecular orbital (LUMO) energy level of the organic compound is less than a LUMO energy level of the donor compound.
  • 5. The opto-electronic device of claim 3, wherein the second layer is in direct contact with the electron transport region.
  • 6. An electronic apparatus comprising the opto-electronic device of claim 1.
  • 7. The electronic apparatus of claim 6, further comprising: a thin-film transistor electrically connected to the first electrode;an emission layer between the first electrode and the second electrode and not overlapping the photoactive layer; anda color filter, a color conversion layer, a touch screen layer, a polarizing layer, or any combination thereof.
  • 8. An electronic device comprising the electronic apparatus of claim 6, wherein the electronic device is one selected from a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor or outdoor lighting and/or signal light, 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 microdisplay, a three-dimensional (3D) display, a virtual or augmented-reality display, a vehicle, a video wall comprising multiple displays tiled together, a theater or stadium screen, a phototherapy device, and a signboard.
  • 9. An organic compound represented by Formula 1:
  • 10. The organic compound of claim 9, wherein the organic compound is represented by one selected from among Formulae 2-1 to 2-3:
  • 11. The organic compound of claim 9, wherein the organic compound is represented by one selected from among Formulae 3-1 to 3-9:
  • 12. The organic compound of claim 9, wherein, in Formulae 1 to 3, X1 and X2 are each independently S or Se.
  • 13. The organic compound of claim 9, wherein, in Formula 1, L1 and L2 are each independently a single bond or a C1-C30 heterocyclic group unsubstituted or substituted with at least one R10a.
  • 14. The organic compound of claim 9, wherein, in Formula 1, L1 and L2 are each independently: a single bond;a thiophenylene group, a 4,6-dimethylene-5,6-dihydro-4H-cyclopentathiophenylene group, a benzofuranylene group, a benzothiophenylene group, a thienofuranylene group, a thienothiophenylene group, a thienofurandionylene group, a thienothiophenedionylene group, a thienothiophenedioxydylene group, a benzodifurantetraonylene group, or a naphthyridinylene group; ora thiophenylene group, a 4,6-dimethylene-5,6-dihydro-4H-cyclopentathiophenylene group, a benzofuranylene group, a benzothiophenylene group, a thienofuranylene group, a thienothiophenylene group, a thienofurandionylene group, a thienothiophenedionylene group, a thienothiophenedioxydylene group, a benzodifurantetraonylene group, or a naphthyridinylene group, each substituted with: —F, —Cl, —Br, —I, —CF3, —NO2, or —CN; or a C1-C12 alkyl group.
  • 15. The organic compound of claim 9, wherein, in Formula 1, R1, R2, Z1, and Z2 are each independently: hydrogen, deuterium, —F, —Cl, —Br, —I, —OH, —CN, —NO2, —CF3, a C1-C60 alkyl group unsubstituted or substituted with at least one R10a, or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a; or —C(═O)(Q1) or —C(═O)O(Q1).
  • 16. The organic compound of claim 9, wherein, in Formula 1, at least one selected from among R1 and R2 is: —F, —Cl, —Br, —I, —CN, —CF3, or a C1-C12 alkyl group; or —C(═O)(Q1) or —C(═O)O(Q1).
  • 17. The organic compound of claim 9, wherein, in Formula 1, at least one selected from among Z1 and Z2 is —F, —Cl, —Br, —I, —OH, —CN, —NO2, or —CF3.
  • 18. The organic compound of claim 9, wherein, in Formula 1, Z1 and Z2 are identical to each other.
  • 19. The organic compound of claim 9, wherein the organic compound is one selected from among Compounds 1 to 24:
Priority Claims (1)
Number Date Country Kind
10-2022-0110320 Aug 2022 KR national