Patent Application
20240188427
This application is claims priority to and the benefit of Korean Patent Application No. 10-2022-0148133, filed on Nov. 8, 2022, in the Korean Intellectual Property Office, the entire content of which is incorporated by reference herein in its entirety.
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.
Opto-electronic devices are devices that convert light energy or a light signal into electrical energy or an electrical signal. Examples of opto-electronic devices include photovoltaic cells or solar cells that convert light energy into electrical energy, photodetectors or light sensors that detect light energy and convert the detected light energy into an electrical signal, and the like.
Electronic apparatuses including opto-electronic devices and organic light-emitting devices have been developed. In an 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, and then 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 used as a fingerprint recognition sensor or the like.
One or more embodiments of the present disclosure include an organic compound having improved light absorption efficiency for a set or specific wavelength, and an opto-electronic device having high light absorption efficiency by including the organic compound. In addition, one or more embodiments include a high-quality electronic apparatus and a high-quality electronic device that include the opto-electronic device.
Additional aspects of embodiments will be set forth in part in the description which follows and, in part, will be apparent from the description, or may be learned by practice of the presented embodiments of the disclosure.
According to one or more embodiments, an opto-electronic device includes a first electrode, a second electrode facing the first electrode, a photoactive layer arranged between the first electrode and the second electrode, and an organic compound represented by Formula 1:
wherein, in Formulae 1 to 3,
CY1 may be a group represented by Formula 2,
CY2 may be a group represented by Formula 3,
CY3 may be a C3-C60 carbocyclic group or a C1-C60 heterocyclic group,
X1 may be O, S, Se, N(R1), or P(═O)R1,
X2 may be O, S, Se, N(R2), or P(═O)R2,
X3 may be O, S, Se, N(R3), or P(═O)R3,
T4 may be *-(L4)b4-(R4)a4,
L4 may be a single bond, a C1-C60 alkylene group unsubstituted or substituted with at least one R10a, a C2-C60 alkenylene group unsubstituted or substituted with at least one R10a, or a C2-C60 alkynylene group unsubstituted or substituted with at least one R10a,
b4 may be an integer from 0 to 3,
R1 to R7 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkenyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkynyl group unsubstituted or substituted with at least one R10a, a C1-C60 alkoxy group unsubstituted or substituted with at least one R10a, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, a C6-C60 aryloxy group unsubstituted or substituted with at least one R10a, a C6-C60 arylthio group unsubstituted or substituted with at least one R10a, a C7-C60 arylalkyl group unsubstituted or substituted with at least one R10a, a C2-C60 heteroarylalkyl group unsubstituted or substituted with at least one R10a, —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), or —P(═O)(Q1)(Q2),
a4 and a5 may each independently be an integer from 0 to 4,
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),
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, or a C1-C60 alkoxy group, each unsubstituted or substituted with deuterium, —F, a hydroxyl group, a cyano group, a nitro group, or any combination thereof, 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 C3-C60 carbocyclic group, a C1-C60 heterocyclic group, or any combination thereof, a C7-C60 arylalkyl group, or a C2-C60 heteroarylalkyl group, and
* indicates a binding site to CY3.
According to one or more embodiments, an electronic apparatus includes the opto-electronic device.
According to one or more embodiments, an electronic device includes the electronic apparatus.
According to one or more embodiments, provided is the organic compound represented by Formula 1.
The above and other aspects and features of certain embodiments of the disclosure will be more apparent from the following description taken in conjunction with the accompanying drawings, in which:
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. In this regard, the present embodiments may have different forms and should not be construed as being limited to the descriptions set forth herein. Accordingly, the embodiments are merely described below, by referring to the figures, to explain aspects of embodiments of the present description. As used herein, the term “and/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 a and b, both a and c, both b and c, all of a, b, and c, or variations thereof.
An aspect of embodiments of the disclosure provides an opto-electronic device including a first electrode, a second electrode facing the first electrode, a photoactive layer arranged 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. The second electrode may be a cathode. The emission layer may include a dopant and a host, and may emit light. The dopant and the host may each be as described herein.
In one or more embodiments, the opto-electronic device may further include a hole transport region arranged between the first electrode and the photoactive layer and an electron transport region arranged 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 first layer may include the organic compound.
For example, the second layer may include fullerene.
For example, the first layer may be referred to as a P-type layer or an electron donor layer. The second layer may be referred to as an N-type 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.
Another aspect of embodiments of the disclosure provides 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 arranged 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, 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 arranged between the first electrode and the emission layer and overlapping the emission layer, and an electron transport region arranged between the second electrode and the emission layer and overlapping the emission layer.
In more detail, each of the hole transport region and the electron transport region may be a common layer, and may overlap both 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.
Another aspect of embodiments of the disclosure provides an electronic device including the electronic apparatus. The electronic device 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.
Another aspect of embodiments of the disclosure provides an organic compound represented by Formula 1:
wherein, in Formulae 1 to 3,
CY1 may be a group represented by Formula 2,
CY2 may be a group represented by Formula 3,
CY3 may be a C3-C60 carbocyclic group or a C1-C60 heterocyclic group,
X1 may be O, S, Se, N(R1), or P(═O)R1,
X2 may be O, S, Se, N(R2), or P(═O)R2,
X3 may be O, S, Se, N(R3), or P(═O)R3,
T4 may be *-(L4)b4-(R4)a4,
L4 may be a single bond, a C1-C60 alkylene group unsubstituted or substituted with at least one R10a, a C2-C60 alkenylene group unsubstituted or substituted with at least one R10a, or a C2-C60 alkynylene group unsubstituted or substituted with at least one R10a,
b4 may be an integer from 0 to 3,
R1 to R7 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkenyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkynyl group unsubstituted or substituted with at least one R10a, a C1-C60 alkoxy group unsubstituted or substituted with at least one R10a, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, a C6-C60 aryloxy group unsubstituted or substituted with at least one R10a, a C6-C60 arylthio group unsubstituted or substituted with at least one R10a, a C7-C60 arylalkyl group unsubstituted or substituted with at least one R10a, a C2-C60 heteroarylalkyl group unsubstituted or substituted with at least one R10a, —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), or —P(═O)(Q1)(Q2),
a4 and a5 may each independently be an integer from 0 to 4,
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),
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, each unsubstituted or substituted with deuterium, —F, a hydroxyl group, a cyano group, a nitro group, or any combination thereof; 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 C3-C60 carbocyclic group, a C1-C60 heterocyclic group, or any combination thereof; a C7-C60 arylalkyl group; or a C2-C60 heteroarylalkyl group, and
* may indicate a binding site to CY3.
In one or more embodiments, the organic compound may be represented by one selected from Formulae 2-1 and 2-2:
wherein, in Formulae 2-1 and 2-2,
CY2, CY3, X1 to X3, T4, L4, b4, R1 to R7, a4, and a5 may each be as defined herein.
For example, 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 Formulae 3-1 to 3-4:
wherein, in Formulae 3-1 to 3-4,
CY1, CY3, X1 to X3, T4, L4, b4, R1 to R7, a4, and a5 may each be as defined herein.
For example, the organic compound may be represented by Formula 3-1.
In one or more embodiments, the organic compound may be represented by one selected from Formulae 1-1 to 1-8:
wherein, in Formulae 1-1 to 1-8,
CY3, X1 to X3, T4, L4, b4, R1 to R7, a4, and a5 may each be as defined herein.
For example, the organic compound may be represented by Formula 1-1.
In one or more embodiments, CY3 in Formula 1 may be a benzene group, a naphthalene group, a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, a quinoline group, or an isoquinoline group.
For example, CY3 in Formula 1 may be a benzene group or a naphthalene group. For example, CY3 in Formula 1 may be a benzene group.
In one or more embodiments, Formula 1 may be represented by one selected from Formulae 4-1 to 4-6:
wherein, in Formulae 4-1 to 4-6,
CY1, CY2, X1 to X3, T4, L4, b4, R1 to R7, a4, and a5 may each be as defined herein.
In one or more embodiments, X1 to X3 in Formulae 1 to 3 may each independently be O, S, or Se.
In one or more embodiments, X1 and X2 in Formulae 1 to 3 may be identical to each other.
For example, X1 to X3 in Formulae 1 to 3 may be identical to each other.
For example, X1 to X3 in Formulae 1 to 3 may each be O, S, or Se.
For example, in Formulae 1 to 3, X1 and X2 may be identical to each other, and X3 may be different from X1 and X2.
For example, in Formulae 1 to 3, X1 and X2 may be identical to each other, X3 may be different from X1 and X2, and X3 may be an element of a higher period in the Periodic Table of Elements than X1 and X2.
For example, in Formulae 1 to 3, when X1 and X2 are each O, X3 may be S or Se. For example, in Formulae 1 to 3, when X1 and X2 are each S, X3 may be Se.
For example, in Formulae 1 to 3, X1 and X2 may be identical to each other, X3 may be different from X1 and X2, and X3 may be an element of a lower period in the Periodic Table of Elements than X1 and X2.
For example, in Formulae 1 to 3, when X1 and X2 are each Se, X3 may be O or S. For example, in Formulae 1 to 3, when X1 and X2 are each S, X3 may be O.
In one or more embodiments, L4 in Formula 1 may be a single bond or a C2-C60 alkenylene group unsubstituted or substituted with at least one R10a.
For example, L4 may be a single bond or a C2-C10 alkenylene group unsubstituted or substituted with at least one R10a. For example, L4 may be a single bond or a vinylidene group unsubstituted or substituted with at least one R10a.
In one or more embodiments, b4 in Formula 1 may be 0 or 1. For example, when b4 is 0, (L4)b4 may be a single bond.
In one or more embodiments, R1 to R7 in Formulae 1 to 3 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkenyl group unsubstituted or substituted with at least one R10a, or a C2-C60 alkynyl group unsubstituted or substituted with at least one R10a.
In one or more embodiments, R4 to R7 in Formulae 1 to 3 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a C1-C60 alkyl group unsubstituted or substituted with at least one R10a, or a C2-C60 alkenyl group unsubstituted or substituted with at least one R10a.
For example, R4 in Formula 1 may be a cyano group or a C2-C60 alkenyl group unsubstituted or substituted with at least one R10a. For example, R4 in Formula 1 may be a cyano group or a C2-C60 alkenyl group substituted with at least one cyano group. For example, R4 in Formula 1 may be a cyano group or a C2-C60 alkenyl group substituted with two or more cyano groups.
For example, R7 in Formula 1 may be hydrogen, deuterium, or a C1-C60 alkyl group unsubstituted or substituted with at least one R10a.
In one or more embodiments, a4 in Formula 1 may be an integer from 0 to 2.
In one or more embodiments, T4 may include two or more cyano groups.
In one or more embodiments, T4 in Formula 1 may be represented by Formula 5:
wherein, in Formula 5,
R41 to R43 may each independently be as defined herein in connection with R4, and * may indicate a binding site to CY3.
For example, R42 and R43 in Formula 5 may be identical to each other. For example, R42 and R43 in Formula 5 may each be a cyano group.
In one or more embodiments, a maximum absorption wavelength of the organic compound may be in a range of about 600 nm to about 660 nm. In more detail, the maximum absorption wavelength of the organic compound may be in a range of about 615 nm to about 645 nm.
In one or more embodiments, a molecular weight of the organic compound may be 700 g/mol or less. For example, the organic compound may be a monomer.
In one or more embodiments, the organic compound may be one selected from Compounds 1 to 32:
The organic compound represented by Formula 1 may have excellent light absorption efficiency at a set or specific wavelength (e.g., a central region of a red wavelength). For example, the organic compound may have a maximum absorption coefficient in a wavelength range of about 600 nm to about 660 nm. Accordingly, the organic compound represented by Formula 1 may have excellent light absorption efficiency for a red wavelength, and an opto-electronic device including the organic compound may have high light absorption efficiency for red wavelength.
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
In
The first electrode 110 may be formed by, for example, depositing and/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. When the first electrode 110 is a transmissive electrode, a material for forming the first electrode 110 may include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or any combination thereof. 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 include 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 consisting of a single layer or a multi-layered structure including a plurality of layers. For example, the first electrode 110 may have a three-layered structure of ITO/Ag/ITO.
The hole transport region 120 may have i) a single-layered structure consisting of a single layer consisting of a single material, ii) a single-layered structure consisting of a single layer 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, 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, the layers of each structure being sequentially stacked from the first electrode 110.
The hole transport region 120 may include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof:
wherein, in Formulae 201 and 202,
L201 to L204 may each independently be a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,
L205 may be *—O—*′, *—S—*′, *—N(Q201)-*′, a C1-C20 alkylene group unsubstituted or substituted with at least one R10a, a C2-C20 alkenylene group unsubstituted or substituted with at least one R10a, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,
xa1 to xa4 may each independently be an integer from 0 to 5,
xa5 may be an integer from 1 to 10,
R201 to R204 and Q201 may each independently be a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,
R201 and R202 may optionally be linked to each other via a single bond, a C1-C5 alkylene group unsubstituted or substituted with at least one R10a, or a C2-C5 alkenylene group unsubstituted or substituted with at least one R10a to form a C8-C60 polycyclic group (e.g., a carbazole group, etc.) unsubstituted or substituted with at least one R10a (e.g., 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.
wherein, in Formulae CY201 to CY217, R10b and R10c may each be as defined herein in connection with 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.
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 groups represented by Formulae CY201 to CY203.
In one or more embodiments, Formula 201 may include at least one selected from groups represented by Formulae CY201 to CY203 and at least one selected from 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 Formulae CY201 to CY203, xa2 may be 0, and R202 may be a group represented by one selected from Formulae CY204 to CY207.
In one or more embodiments, each of Formulae 201 and 202 may not include a group represented by one selected from Formulae CY201 to CY203.
In one or more embodiments, each of Formulae 201 and 202 may not include a group represented by one selected from Formulae CY201 to CY203, and may include at least one selected from groups represented by Formulae CY204 to CY217.
In one or more embodiments, each of Formulae 201 and 202 may not include a group represented by one selected from Formulae CY201 to CY217.
For example, the hole transport region 120 may include one selected from Compounds HT1 to HT46, m-MTDATA, TDATA, 2-TNATA, NPB(NPD), p-NPB, TPD, Spiro-TPD, Spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphor sulfonic acid (PANI/CSA) and polyaniline/poly(4-styrenesulfonate) (PANI/PSS), or any combination thereof:
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, suitable or 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 described above, a charge-generation material for the improvement of conductive characteristics (e.g., electrically conductive characteristics). 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 consisting of a charge-generation material).
The charge-generation material may be, for example, a p-dopant.
For example, the lowest unoccupied molecular orbital (LUMO) energy level of the p-dopant may be −3.5 eV or less.
In one or more embodiments, the p-dopant may include a quinone derivative, a cyano group-containing compound, a compound containing element EL1 and element EL2, or any combination thereof.
Examples of the quinone derivative are TCNQ, F4-TCNQ, and the like.
Examples of the cyano group-containing compound may include HAT-CN, a compound represented by Formula 221, and the like:
wherein, in Formula 221,
R221 to R223 may each independently be a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, and
at least one selected from 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.
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 the like.
Examples of the metalloid may include silicon (Si), antimony (Sb), tellurium (Te), and the like.
Examples of the non-metal may include oxygen (O), halogen (e.g., F, Cl, Br, I, etc.), and the like.
Examples of the compound containing element EL1 and element EL2 may include a metal oxide, a metal halide (e.g., a metal fluoride, a metal chloride, a metal bromide, a metal iodide, etc.), a metalloid halide (e.g., a metalloid fluoride, a metalloid chloride, a metalloid bromide, a metalloid iodide, etc.), a metal telluride, or any combination thereof.
Examples of the metal oxide may include a tungsten oxide (e.g., WO, W2O3, WO2, WO3, W2O5, etc.), a vanadium oxide (e.g., VO, V2O3, VO2, V2O5, etc.), a molybdenum oxide (e.g., MoO, Mo2O3, MoO2, MoO3, Mo2O5, etc.), a rhenium oxide (e.g., ReO3, etc.), and the like.
Examples of the metal halide may include an alkali metal halide, an alkaline earth metal halide, a transition metal halide, a post-transition metal halide, a lanthanide metal halide, and the like.
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 the like.
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 the like.
Examples of the transition metal halide may include a titanium halide (e.g., TiF4, TiCl4, TiBr4, TiI4, etc.), a zirconium halide (e.g., ZrF4, ZrCl4, ZrBr4, ZrI4, etc.), a hafnium halide (e.g., HfF4, HfCl4, HfBr4, Hfl4, etc.), a vanadium halide (e.g., VF3, VCl3, VBr3, VI3, etc.), a niobium halide (e.g., NbF3, NbCl3, NbBr3, NbI3, etc.), a tantalum halide (e.g., TaF3, TaCl3, TaBr3, TaI3, etc.), a chromium halide (e.g., CrF3, CrO3, CrBr3, CrI3, etc.), a molybdenum halide (e.g., MoF3, MoCl3, MoBr3, MoI3, etc.), a tungsten halide (e.g., WF3, WCl3, WBr3, WI3, etc.), a manganese halide (e.g., MnF2, MnCl2, MnBr2, MnI2, etc.), a technetium halide (e.g., TcF2, TcCl2, TcBr2, TcI2, etc.), a rhenium halide (e.g., ReF2, ReCl2, ReBr2, ReI2, etc.), a ferrous halide (e.g., FeF2, FeCl2, FeBr2, FeI2, etc.), a ruthenium halide (e.g., RuF2, RuCl2, RuBr2, RuI2, etc.), an osmium halide (e.g., OsF2, OsCl2, OsBr2, OsI2, etc.), a cobalt halide (e.g., CoF2, COCl2, CoBr2, CoI2, etc.), a rhodium halide (e.g., RhF2, RhCl2, RhBr2, RhI2, etc.), an iridium halide (e.g., IrF2, IrCl2, IrBr2, IrI2, etc.), a nickel halide (e.g., NiF2, NiCl2, NiBr2, NiI2, etc.), a palladium halide (e.g., PdF2, PdCl2, PdBr2, PdI2, etc.), a platinum halide (e.g., PtF2, PtCl2, PtBr2, PtI2, etc.), a cuprous halide (e.g., CuF, CuCl, CuBr, CuI, etc.), a silver halide (e.g., AgF, AgCl, AgBr, AgI, etc.), a gold halide (e.g., AuF, AuCl, AuBr, AuI, etc.), and the like.
Examples of the post-transition metal halide may include a zinc halide (e.g., ZnF2, ZnCl2, ZnBr2, ZnI2, etc.), an indium halide (e.g., InI3, etc.), a tin halide (e.g., SnI2, etc.), and the like.
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 the like.
Examples of the metalloid halide may include an antimony halide (e.g., SbCl5, etc.) and the like.
Examples of the metal telluride may include an alkali metal telluride (e.g., Li2Te, Na2Te, K2Te, Rb2Te, Cs2Te, etc.), an alkaline earth metal telluride (e.g., BeTe, MgTe, CaTe, SrTe, BaTe, etc.), a 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.), a post-transition metal telluride (e.g., ZnTe, etc.), a lanthanide metal telluride (e.g., LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, etc.), and the like.
The light-emitting device 10 may include the emission layer 130 arranged on the hole transport region 120.
The emission layer 130 may further include, in addition to various 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 arranged 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. 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 together with each other in a single layer to emit 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.
An amount of the dopant in the emission layer 130 may be in a range of 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 luminescence characteristics may be obtained without a substantial increase in driving voltage.
The host may include a compound represented by Formula 301:
[Ar301]xb11-[(L301)xb1-R301]xb21, Formula 301
wherein, in Formula 301,
Ar301 and L301 may each independently be a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,
xb11 may be 1, 2, or 3,
xb1 may be an integer from 0 to 5,
R301 may be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkenyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkynyl group unsubstituted or substituted with at least one R10a, a C1-C60 alkoxy group unsubstituted or substituted with at least one R10a, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, —Si(Q301)(Q302)(Q303), —N(Q301)(Q302), —B(Q301)(Q302), —C(═O)(Q301), —S(═O)2(Q301), or —P(═O)(Q301)(Q302),
xb21 may be an integer from 1 to 5, and
Q301 to Q303 may each be as defined herein in connection with Q1.
For example, 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:
wherein, 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 as defined herein,
L302 to L304 may each independently be as defined herein in connection with L301,
xb2 to xb4 may each independently be as defined herein in connection with xb1, and
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, 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 one selected from 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-butylanthracene (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), or any combination thereof:
The phosphorescent dopant may include at least one transition metal as a central metal.
The phosphorescent dopant may include a monodentate ligand, a bidentate ligand, a tridentate ligand, a tetradentate ligand, a pentadentate ligand, a hexadentate ligand, or any combination thereof.
The phosphorescent dopant may be electrically neutral.
For example, the phosphorescent dopant may include an organometallic compound represented by Formula 401:
M(L401)xc1(L402)xc2 Formula 401
wherein, 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,
Q411 to Q414 may each be as defined herein in connection with Q1,
R401 and R402 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C20 alkyl group unsubstituted or substituted with at least one R10a, a C1-C20 alkoxy group unsubstituted or substituted with at least one R10a, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, —Si(Q401)(Q402)(Q403), —N(Q401)(Q402), —B(Q401)(Q402), —C(═O)(Q401), —S(═O)2(Q401), or —P(═O)(Q401)(Q402),
Q401 to Q403 may each be as defined herein in connection with 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) X401 and X402 may each 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 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 as defined herein in connection with T401.
L402 in Formula 401 may be an organic ligand. For example, L402 may include a halogen group, a diketone group (e.g., an acetylacetonate group), a carboxylic acid group (e.g., a picolinate group), —C(═O) group, an isonitrile group, a —CN group, a phosphorus-containing group (e.g., a phosphine group, a phosphite group, etc.), or any combination thereof.
The phosphorescent dopant may include, for example, one selected from Compounds PD1 to PD39 or any combination thereof:
The fluorescent dopant may include an amine group-containing compound, a styryl group-containing compound, or any combination thereof.
For example, the fluorescent dopant may include a compound represented by Formula 501:
wherein, in Formula 501,
Ar501, L501 to L503, R501, and R502 may each independently be a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,
xd1 to xd3 may each independently be 0, 1, 2, or 3, and
xd4 may be 1, 2, 3, 4, 5, or 6.
For example, Ar501 in Formula 501 may be a condensed cyclic group (e.g., an anthracene group, a chrysene group, a pyrene group, etc.) in which three or more monocyclic groups are condensed together with each other.
In one or more embodiments, xd4 in Formula 501 may be 2.
For example, the fluorescent dopant may include one selected from Compounds FD1 to FD37, DPVBi and DPAVBi, or any combination thereof:
The emission layer 130 may include a delayed fluorescence material.
In the present specification, 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 0 eV or more and 0.5 eV or less. 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, 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 ii) a material including a C8-C60 polycyclic group in which two or more cyclic groups are condensed together while sharing boron (B).
Examples of the delayed fluorescence material may include at least one selected from Compounds DF1 to DF14:
The emission layer 130 may include a quantum dot.
The term “quantum dot” as used herein refers to a crystal of a semiconductor compound, and may include any suitable material capable of emitting light of various 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, and/or any suitable process similar thereto.
The wet chemical process is a method including mixing a precursor material together with an organic solvent and then growing a quantum dot particle crystal. When the crystal grows, the organic solvent naturally acts as a dispersant coordinated on the surface of the quantum dot crystal and controls the growth of the crystal so that the growth of quantum dot particles can be controlled 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.
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, and/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, and/or MgZnS; a quaternary compound, such as CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, and/or HgZnSTe; or any combination thereof.
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, and/or InSb; a ternary compound, such as GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNP, InAlP, InNAs, InNSb, InPAs, and/or InPSb; a quaternary compound, such as GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, and/or InAlPSb; or any combination thereof. In one or more embodiments, the Group III-V semiconductor compound may further include a Group II element. Examples of the Group III-V semiconductor compound further including a Group II element may include InZnP, InGaZnP, InAlZnP, and the like.
Examples of the Group III-VI semiconductor compound may include: a binary compound, such as GaS, GaSe, Ga2Se3, GaTe, InS, InSe, In2S3, In2Se3, and/or InTe; a ternary compound, such as InGaS3 and/or InGaSe3; or any combination thereof.
Examples of the Group I-III-VI semiconductor compound may include: a ternary compound, such as AgInS, AgInS2, CuInS, CuInS2, CuGaO2, AgGaO2, and/or AgAlO2; or any combination thereof.
Examples of the Group IV-VI semiconductor compound may include: a binary compound, such as SnS, SnSe, SnTe, PbS, PbSe, and/or PbTe; a ternary compound, such as SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, and/or SnPbTe; a quaternary compound, such as SnPbSSe, SnPbSeTe, and/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 and/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 uniform concentration or non-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 uniform (e.g., 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 or reduces chemical degeneration of the core to maintain semiconductor characteristics, and/or as a charging layer that imparts electrophoretic characteristics to the quantum dot. The shell may be a single layer or a multi-layer. The interface between the core and the shell may have a concentration gradient in which the concentration of an element existing in the shell decreases along a direction toward the center of the core.
Examples of the shell of the quantum dot may include an oxide of metal, metalloid, and/or non-metal, a semiconductor compound, or any combination thereof. Examples of the oxide of metal, metalloid, and/or non-metal may include: a binary compound, such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4, and/or NiO; a ternary compound, such as MgAl2O4, CoFe2O4, NiFe2O4, and/or CoMn2O4; or any combination thereof. 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 and/or color reproducibility may be improved. In addition, because the light emitted through the quantum dot is emitted in all directions, the wide viewing angle may be improved.
In addition, the quantum dot may be in the form of a spherical particle, a pyramidal particle, a multi-arm particle, a cubic nanoparticle, a nanotube particle, a nanowire particle, a nanofiber particle, and/or a nanoplate particle.
Because the energy band gap may be adjusted by controlling the size of the quantum dot, light having various suitable wavelength bands may be obtained from an emission layer including the quantum dot. Accordingly, by using quantum dots of different sizes, a light-emitting device that emits light of various suitable wavelengths may be implemented. In more detail, the size of the quantum dot may be selected to emit red, green and/or blue light. In addition, the size of the quantum dot may be configured to emit white light by combining light of various suitable colors.
The opto-electronic device 30 may include the photoactive layer 135 arranged 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 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.
The electron transport region 140 may be arranged 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 consisting of a single layer consisting of a single material, ii) a single-layered structure 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 have an electron transport layer/electron injection layer structure, a hole blocking layer/electron transport layer/electron injection layer structure, an electron control layer/electron transport layer/electron injection layer structure, or a buffer layer/electron transport layer/electron injection layer structure, the layers of each structure being sequentially stacked from the emission layer 130.
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, the electron transport region 140 may include a compound represented by Formula 601:
[Ar601]xe11-[(L601)xe1-R601]xe21, Formula 601
wherein, in Formula 601,
Ar601 and L601 may each independently be a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,
xe11 may be 1, 2, or 3,
xe1 may be 0, 1, 2, 3, 4, or 5,
R601 may be a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, —Si(Q601)(Q602)(Q603), —C(═O)(Q601), —S(═O)2(Q601), or —P(═O)(Q601)(Q602),
Q601 to Q603 may each be as defined herein in connection with Q1,
xe21 may be 1, 2, 3, 4, or 5, and
at least one selected from 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 anthracene group unsubstituted or substituted with at least one R10a.
In one or more embodiments, the electron transport region 140 may include a compound represented by Formula 601-1:
wherein, in Formula 601-1,
X614 may be N or C(R614), X615 may be N or C(R615), X616 may be N or C(R616), and at least one selected from X614 to X616 may be N,
L611 to L613 may each be as defined herein in connection with L601,
xe611 to xe613 may each be as defined herein in connection with xe1,
R611 to R613 may each be as defined herein in connection with R601 and
R614 to R616 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a.
For example, xe1 and xe611 to xe613 in Formulae 601 and 601-1 may each independently be 0, 1, or 2.
The electron transport region 140 may include one selected from Compounds ET1 to ET45, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq3, BAlq, TAZ and NTAZ, or any combination thereof:
A thickness of the electron transport region 140 may be in a range of 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 thicknesses 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, suitable or satisfactory electron transporting characteristics may be obtained without a substantial increase in driving voltage.
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, and/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, and/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, the metal-containing material may include a Li complex. The Li complex may include, for example, Compound ET-D1 (Liq) and/or ET-D2:
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 consisting of a single layer consisting of a single material, ii) a single-layered structure 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 include oxides, halides (e.g., fluorides, chlorides, bromides, iodides, etc.), and/or tellurides of the alkali metal, the alkaline earth metal, and/or the rare earth metal, or any combination thereof.
The alkali metal-containing compound may include an alkali metal oxide, such as Li2O, Cs2O, and/or K2O, an alkali metal halide, such as LiF, NaF, CsF, KF, LiI, NaI, CsI, and/or KI, or any combination thereof. The alkaline earth metal-containing compound may include an alkaline earth metal compound (e.g., oxide), such as BaO, SrO, CaO, BaxSr1-xO (wherein x is a real number satisfying the condition of 0<x<1), and/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. 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 selected from ions of the alkali metal, the alkaline earth metal, and the rare earth metal and ii), as 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 consist of (e.g., include) an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof, as described 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 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, suitable or satisfactory electron injection characteristics may be obtained without a substantial increase in driving voltage.
The second electrode 150 may be arranged on the electron transport region 140. The second electrode 150 may be a cathode, which is an electron injection electrode, and as a material for forming the second electrode 150, a metal, an alloy, an electrically conductive compound, or any combination thereof, each having a low work function, may be used.
The second electrode 150 may include 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.
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 more detail, 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 one or more 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 one or more 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. Accordingly, 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 of 1.6 or more (at a wavelength of 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 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 the first capping layer and the second capping layer may each independently include an amine group-containing compound.
For example, at least one selected from 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 the first capping layer and the second capping layer may each independently include one selected from Compounds HT28 to HT33, one selected from Compounds CP1 to CP6, p-NPB, or any combination thereof:
A film may be, for example, an optical member (or a light control member) (e.g., a color filter, a color conversion member, a capping layer, a light extraction efficiency improvement layer, a selective light absorption layer, a polarizing layer, a quantum dot-containing layer, etc.), a light blocking member (e.g., a light reflection layer, a light absorption layer, etc.), a protection member (e.g., an insulating layer, a dielectric layer, etc.), and/or the like.
The light-emitting device 10 and the opto-electronic device 30 may be included in various 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, the light emitted from the light-emitting device 10 may be blue light or white light. Further details of the light-emitting device 10 may be 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 further 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 that emits a first color light, a second area that emits a second color light, and/or a third area that emits a 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, the first color light may be red light, the second color light may be green light, and the third color light may be blue light. For example, the color filter areas (or the color conversion areas) may include quantum dots. In more detail, the first area may include a red quantum dot, the second area may include a green quantum dot, and the third area may not include a quantum dot. Further details of 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 (e.g., a light scatterer).
For example, the light-emitting device 10 may emit a first light, the first area may absorb the first light to emit a first-first color light, the second area may absorb the first light to emit a second-first color light, and the third area may absorb the first light to emit a 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 more detail, the first light may be blue light, the first-first color light may be red light, the second-first color light may be green light, and the third-first color light may be blue light.
The electronic apparatus may further include a thin-film transistor, in addition to the 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 selected from the source electrode and the drain electrode may be electrically connected to one selected from the first electrode 110 and 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 penetration of ambient air and/or moisture into the light-emitting device 10. The sealing portion may be a sealing substrate including a transparent glass substrate and/or a plastic substrate. The sealing portion may be a thin-film encapsulation layer including at least one layer of an organic layer and/or an inorganic layer. When the sealing portion is a thin-film encapsulation layer, the electronic apparatus may be flexible.
Various suitable 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 use of the electronic apparatus. Examples of the functional layers may include a touch screen layer, a polarizing layer, and/or the like. The touch screen layer may be a pressure-sensitive touch screen layer, a capacitive touch screen layer, and/or an infrared touch screen layer. The authentication apparatus may be, for example, a biometric authentication apparatus that authenticates an individual by using biometric information of a living body (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 various suitable displays, light sources, lighting, personal computers (e.g., mobile personal computers), 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, and/or endoscope displays), fish finders, various suitable measuring instruments, meters (e.g., meters for a vehicle, an aircraft, and/or a vessel), projectors, and/or the like.
The light-emitting device 10 may be included in various 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 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.
The electronic apparatus of
The substrate 100 may be a flexible substrate, a glass substrate, and/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.
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 a 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 and/or polyacrylic organic film. In one or more 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 on the second electrode 150. The capping layer 170 may 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-based 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.
The electronic apparatus of
The electronic device 1 may include a display area DA and a non-display area NDA outside the display area DA. 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 is 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 (or x-direction) and in the y-axis direction (or y-direction) and a thickness in the z-axis direction (or z-direction). For example, as shown in
Referring to
The vehicle 1000 may travel on a road and/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 prime mover apparatus, a bicycle, and/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 useful or 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/or 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/or a display apparatus 2.
The side window glass 1100 and the front window glass 1200 may be partitioned by a pillar arranged between the side window glass 1100 and the front window glass 1200.
The side window glass 1100 may be installed on the side of the vehicle 1000. In one or more embodiments, the side window glass 1100 may be installed on a door of the vehicle 1000. A plurality of side window glasses 1100 may be provided and may face each other. In one or more embodiments, the side window glass 1100 may include a first side window glass 1110 and a second side window glass 1120. In one or more embodiments, the first side window glass 1110 may be arranged adjacent to the cluster 1400. The second side window glass 1120 may be arranged adjacent to the passenger seat dashboard 1600.
In one or more embodiments, the side window glasses 1100 may be 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 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 view of the rear 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 turn indicator, a high beam indicator, a warning lamp, a seat belt warning lamp, an odometer, a hodometer, an automatic transmission selection lever indicator, a door open warning lamp, an engine oil warning lamp, and/or a low fuel warning lamp.
The center fascia 1500 may include a control panel including a plurality of buttons for adjusting an audio apparatus, an air conditioning apparatus, and/or a heater of a seat. The center fascia 1500 may be arranged on one side of the cluster 1400.
The passenger seat dashboard 1600 may be 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 one or more 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 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, as the display apparatus 2 according to one or more embodiments, an organic light-emitting display apparatus including the light-emitting device according to one or more embodiments will be described as an example, but various suitable types or kinds of display apparatuses as described above may be used in embodiments.
Referring to
Referring to
Referring to
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 using 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 10−8 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, in which a first moiety represented by Formula 1 and a second moiety represented by Formula 2 are bonded together, has excellent heat resistance, when the first layer 131 included in the photoactive layer 135 is formed using the organic compound by vacuum deposition, the first layer 131 may be easily formed without defects.
The term “C3-C60 carbocyclic group” as used 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 used herein refers to a cyclic group that has 1 to 60 carbon atoms and further has, in addition to carbon, a heteroatom as a ring-forming atom. The C3-C60 carbocyclic group and the C1-C60 heterocyclic group may each be a monocyclic group consisting of one ring or a polycyclic group in which two or more rings are condensed together with each other. For example, the C1-C60 heterocyclic group may have 3 to 61 ring-forming atoms.
The “cyclic group” as used herein may include both the C3-C60 carbocyclic group and the C1-C60 heterocyclic group.
The term “π electron-rich C3-C60 cyclic group” as used herein refers to a cyclic group that has 3 to 60 carbon atoms and does not include *—N=*′ as a ring-forming moiety, and the term “π electron-deficient nitrogen-containing C1-C60 cyclic group” as used herein refers to a heterocyclic group that has 1 to 60 carbon atoms and includes *—N=*′ as a ring-forming moiety.
For example, the C3-C60 carbocyclic group may be i) a group T1 or ii) a condensed cyclic group in which two or more groups T1 are condensed together 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 together with each other, or iii) a condensed cyclic group in which at least one group T2 and at least one group T1 are condensed together 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 together with each other, iii) a group T3, iv) a condensed cyclic group in which two or more groups T3 are condensed together with each other, or v) a condensed cyclic group in which at least one group T3 and at least one group T1 are condensed together 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 together with each other, iii) a condensed cyclic group in which at least one group T4 and at least one group T1 are condensed together with each other, iv) a condensed cyclic group in which at least one group T4 and at least one group T3 are condensed together 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 together 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 1H-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 term “cyclic group,” “C3-C60 carbocyclic group,” “C1-C60 heterocyclic group,” “π electron-rich C3-C60 cyclic group,” or “π electron-deficient nitrogen-containing C1-C60 cyclic group” as used herein refers to a group condensed together 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 used. For example, the “benzene group” may be a benzo group, a phenyl group, a phenylene group, or the like, which may be easily understood by one of ordinary skill in the art according to the structure of a formula including the “benzene group.”
Examples of the monovalent C3-C60 carbocyclic group and 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 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 used herein refers to a linear or branched aliphatic saturated hydrocarbon monovalent group that has 1 to 60 carbon atoms, and 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 the like. The term “C1-C60 alkylene group” as used herein refers to a divalent group having substantially the same structure as the C1-C60 alkyl group.
The term “C2-C60 alkenyl group” as used herein refers to a monovalent hydrocarbon group having at least one carbon-carbon double bond in the middle or at the terminus of the C2-C60 alkyl group, and examples thereof may include an ethenyl group, a propenyl group, a butenyl group, and the like. The term “C2-C60 alkenylene group” as used herein refers to a divalent group having substantially the same structure as the C2-C60 alkenyl group.
The term “C2-C60 alkynyl group” as used herein refers to a monovalent hydrocarbon group having at least one carbon-carbon triple bond in the middle or at the terminus of the C2-C60 alkyl group, and examples thereof may include an ethynyl group, a propynyl group, and the like. The term “C2-C60 alkynylene group” as used herein refers to a divalent group having substantially the same structure as the C2-C60 alkynyl group.
The term “C1-C60 alkoxy group” as used herein refers to a monovalent group represented by —OA101 (wherein A101 is the C1-C60 alkyl group), and examples thereof may include a methoxy group, an ethoxy group, an isopropyloxy group, and the like.
The term “C3-C10 cycloalkyl group” as used herein refers to a monovalent saturated hydrocarbon cyclic group having 3 to 10 carbon atoms, and examples thereof 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 the like. The term “C3-C10 cycloalkylene group” as used herein refers to a divalent group having substantially the same structure as the C3-C10 cycloalkyl group.
The term “C1-C10 heterocycloalkyl group” as used herein refers to a monovalent cyclic group that has 1 to 10 carbon atoms and further includes, in addition to carbon atoms, at least one heteroatom as a ring-forming atom, and examples thereof may include a 1,2,3,4-oxatriazolidinyl group, a tetrahydrofuranyl group, a tetrahydrothiophenyl group, and the like. The term “C1-C10 heterocycloalkylene group” as used herein refers to a divalent group having substantially the same structure as the C1-C10 heterocycloalkyl group.
The term “C3-C10 cycloalkenyl group” as used herein refers to a monovalent cyclic group that has 3 to 10 carbon atoms and at least one carbon-carbon double bond in the ring thereof and no aromaticity (e.g., is not aromatic), and examples thereof may include a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, and the like. The term “C3-C10 cycloalkenylene group” as used herein refers to a divalent group having substantially the same structure as the C3-C10 cycloalkenyl group.
The term “C1-C10 heterocycloalkenyl group” as used herein refers to a monovalent cyclic group that has 1 to 10 carbon atoms, at least one heteroatom as a ring-forming atom, in addition to carbon atoms, and at least one double bond in the ring thereof. Examples of the C1-C10 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 the like. The term “C1-C10 heterocycloalkenylene group” as used herein refers to a divalent group having substantially the same structure as the C1-C10 heterocycloalkenyl group.
The term “C6-C60 aryl group” as used herein refers to a monovalent group having a carbocyclic aromatic system of 6 to 60 carbon atoms, and the term “C6-C60 arylene group” as used herein refers to a divalent group having a carbocyclic aromatic system of 6 to 60 carbon atoms. Examples of the C6-C60 aryl group 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 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 together with each other.
The term “C1-C60 heteroaryl group” as used herein refers to a monovalent group having a heterocyclic aromatic system of 1 to 60 carbon atoms, and further including, in addition to carbon atoms, at least one heteroatom, as ring-forming atoms, and the term “C1-C60 heteroarylene group” as used herein refers to a divalent group having a heterocyclic aromatic system of 1 to 60 carbon atoms, and further including, in addition to carbon atoms, at least one heteroatom, as ring-forming atoms. 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 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 together with each other.
The term “monovalent non-aromatic condensed polycyclic group” as used herein refers to a monovalent group that has two or more rings condensed together 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 (e.g., is not aromatic). 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 the like. The term “divalent non-aromatic condensed polycyclic group” as used herein refers to a divalent group having substantially the same structure as the monovalent non-aromatic condensed polycyclic group.
The term “monovalent non-aromatic condensed heteropolycyclic group” as used herein refers to a monovalent group that has two or more rings condensed together 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 (e.g., is not aromatic). 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 naphthoindolyl group, an isoindolyl group, a benzoisoindolyl group, a naphthoisoindolyl group, a benzosilolyl group, a benzothiophenyl group, a benzofuranyl group, a carbazolyl group, a dibenzosilolyl group, a dibenzothiophenyl group, a dibenzofuranyl group, an azacarbazolyl group, an azafluorenyl group, an azadibenzosilolyl group, an azadibenzothiophenyl group, an azadibenzofuranyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzopyrazolyl group, a benzimidazolyl group, a benzoxazolyl group, a benzothiazolyl group, a benzoxadiazolyl group, a benzothiadiazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an imidazotriazinyl group, an imidazopyrazinyl group, an imidazopyridazinyl group, an 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 the like. The term “divalent non-aromatic condensed heteropolycyclic group” as used herein refers to a divalent group having substantially the same structure as the monovalent non-aromatic condensed heteropolycyclic group.
The term “C6-C60 aryloxy group” as used herein refers to —OA102 (wherein A102 is the C6-C60 aryl group), and the term “C6-C60 arylthio group” as used herein refers to —SA103 (wherein A103 is the C6-C60 aryl group).
The term “C7-C60 arylalkyl group” as used herein refers to -A104A105 (wherein A104 is a C1-C54 alkylene group, and A105 is a C6-C59 aryl group), and the term “C2-C60 heteroarylalkyl group” as used herein refers to -A106A107 (wherein A106 is a C1-C59 alkylene group, and A107 is a C1-C59 heteroaryl group).
The term “R10a” as used herein refers to:
deuterium, —F, —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 used herein may each independently be: hydrogen; deuterium; —F; —CI; —Br; —I; a hydroxyl group; a cyano group; a nitro group; a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group, each unsubstituted or substituted with deuterium, —F, a hydroxyl group, a cyano group, a nitro group, or any combination thereof; 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 C3-C60 carbocyclic group, a C1-C60 heterocyclic group, or any combination thereof; a C7-C60 arylalkyl group; or a C2-C60 heteroarylalkyl group.
The term “heteroatom” as used herein refers to any suitable atom other than a carbon atom. Examples of the heteroatom may include O, S, N, P, Si, B, Ge, Se, or any combination thereof.
The term “third-row transition metal” as used herein may include hafnium (Hf), tantalum (Ta), tungsten (W), rhenium (Re), osmium (Os), iridium (Ir), platinum (Pt), gold (Au), and the like.
The term “Ph” as used herein refers to a phenyl group, the term “Me” as used herein refers to a methyl group, the term “Et” as used herein refers to an ethyl group, the term “tert-Bu” or “But” as used herein refers to a tert-butyl group, and the term “OMe” as used herein refers to a methoxy group.
The term “biphenyl group” as used 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 used 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 used 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 used 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, organic compounds according to embodiments and light-emitting devices and opto-electronic devices according to embodiments will be described in more detail with reference to Synthesis Examples and Examples. The wording “B was used instead of A” used in describing Synthesis Examples means that an identical molar equivalent of B was used in place of an identical molar equivalent of A.
In an argon atmosphere, 4-isobutyl-4H-benzo[4,5]thieno[3,2-b]thieno[2,3-d]pyrrole (11.4 mL, 40 mmol) was dissolved in 40 mL of tetrahydrofuran (THF), and the resultant mixture was cooled to −78° C. n-BuLi (27.5 mL, 1.6M in hexanes, 44 mmol) was added dropwise thereto for 10 minutes, and the mixture was stirred for 40 minutes. Then, the mixture was added dropwise to 20 mL of a THF solution of B(O-i-Pr)3 (13.9 mL, 60 mmol), which had been cooled to 0° C., for 15 minutes. The mixture was stirred at the same temperature for 1 hour and then at room temperature for 17 hours. After completion of the reaction, the solvent was removed therefrom under reduced pressure, and the reaction product was separated and purified by column chromatography using ethyl acetate and hexane to obtain Intermediate 4-a (6.6 g, 70%).
The obtained compound was identified by electro-spray ionization liquid chromatography-mass spectrometry (ESI-LCMS) as Intermediate 4-a. (ESI-LCMS: [M]+: C16H16BNO2S2. 329.07)
In an argon atmosphere, 4 mL of an ethanol (EtOH) solution of Intermediate 4-a (2.6 g, 8.0 mmol) and 3.6 mL of a 2M aqueous sodium carbonate (Na2CO3) solution were added to 10 mL of a toluene solution of 4-iodobenzo[c][1,2,5]thiadiazole (1.0 g, 4.0 mmol), and the resultant mixture was purged with nitrogen while being degassed. Then, Pd(PPh3)4 (0.3 g, 0.3 mmol) was added thereto, and the mixture was stirred at 80° C. for 12 hours. After cooling, an extraction process was performed thereon using water (500 mL) and ethyl acetate (300 mL) to collect an organic layer, which was then dried using anhydrous MgSO4 and filtered. The filtered solution was placed under reduced pressure to remove the solvent therefrom, and the obtained solid was separated and purified by column chromatography using CH2Cl2 and hexane to obtain Intermediate 4-b (1.0 g, 2.5 mmol, 60%).
The obtained compound was identified by ESI-LCMS as Intermediate 4-b. (ESI-LCMS: [M]+: C22H17N3S3. 419.06)
In an argon atmosphere, Intermediate 4-b (1.0 g, 2.3 mmol) was dissolved in 50 mL of THF, and the resultant mixture was cooled to −78° C. n-BuLi (1.9 mL, 1.6M in hexanes, 3.0 mmol) was added thereto, and the mixture was stirred for 30 minutes. Then, dimethylformamide (DMF) (0.2 mL, 3.0 mmol) was added thereto, and the mixture was stirred at the same temperature for 30 minutes and then at room temperature for 10 hours. After cooling, an extraction process was performed thereon using water (500 mL) and ethyl acetate (300 mL) to collect an organic layer, which was then dried using anhydrous MgSO4 and filtered. The filtered solution was placed under reduced pressure to remove the solvent therefrom, and the obtained solid was separated and purified by column chromatography using CH2Cl2 and hexane to obtain Intermediate 4-c (0.6 g, 1.3 mmol, 58%).
The obtained compound was identified by ESI-LCMS as Intermediate 4-c. (ESI-LCMS: [M]+: C23H17N3OS3. 447.05)
In an argon atmosphere, Intermediate 4-c (0.18 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 mixture was stirred at room temperature for 35 minutes and then concentrated under reduced pressure. The obtained solid was separated and purified by column chromatography using CH2Cl2 and hexane to obtain Compound 4 (0.13 g, 0.27 mmol, 61%).
The obtained compound was identified by ESI-LCMS as Compound 4. (ESI-LCMS: [M]+: C26H17N5S3. 495.06)
In an argon atmosphere, 4-propyl-4H-benzofuro[3,2-b]furo[2,3-d]pyrrole (9.6 mL, 40 mmol) was dissolved in 40 mL of THF, and the resultant mixture was cooled to −78° C. n-BuLi (27.5 mL, 1.6M in hexanes, 44 mmol) was added dropwise thereto for 10 minutes, and the mixture was stirred for 40 minutes. Then, the mixture was added dropwise to 20 mL of a THF solution of B(O-i-Pr)3 (13.9 mL, 60 mmol), which had been cooled to 0° C., for 15 minutes. The mixture was stirred at the same temperature for 1 hour and then at room temperature for 17 hours. After completion of the reaction, the solvent was removed therefrom under reduced pressure, and the reaction product was separated and purified by column chromatography using ethyl acetate and hexane to obtain Intermediate 7-a (5.6 g, 68%).
The obtained compound was identified by ESI-LCMS as Intermediate 7-a. (ESI-LCMS: [M]+: C15H14BNO4. 283.10)
In an argon atmosphere, 4 mL of an ethanol (EtOH) solution of Intermediate 7-a (2.3 g, 8.0 mmol) and 3.6 mL of a 2M aqueous sodium carbonate (Na2CO3) solution were added to 10 mL of a toluene solution of 4-iodobenzo[c][1,2,5]oxadiazole (1.0 g, 4.0 mmol), and the resultant mixture was purged with nitrogen while being degassed. Then, Pd(PPh3)4 (0.3 g, 0.3 mmol) was added thereto, and the mixture was stirred at 80° C. for 12 hours. After cooling, an extraction process was performed thereon using water (500 mL) and ethyl acetate (300 mL) to collect an organic layer, which was then dried using anhydrous MgSO4 and filtered. The filtered solution was placed under reduced pressure to remove the solvent therefrom, and the obtained solid was separated and purified by column chromatography using CH2Cl2 and hexane to obtain Intermediate 7-b (0.9 g, 2.5 mmol, 62%).
The obtained compound was identified by ESI-LCMS as Intermediate 7-b. (ESI-LCMS: [M]+: C21H15N3O3. 357.11)
In an argon atmosphere, Intermediate 7-b (0.8 g, 2.3 mmol) was dissolved in 50 mL of THF, and the resultant mixture was cooled to −78° C. n-BuLi (1.9 mL, 1.6M in hexanes, 3.0 mmol) was added thereto, and the mixture was stirred for 30 minutes. Then, DMF (0.2 mL, 3.0 mmol) was added thereto, and the mixture was stirred at the same temperature for 30 minutes and then at room temperature for 10 hours. After cooling, an extraction process was performed thereon using water (500 mL) and ethyl acetate (300 mL) to collect an organic layer, which was then dried using anhydrous MgSO4 and filtered. The filtered solution was placed under reduced pressure to remove the solvent therefrom, and the obtained solid was separated and purified by column chromatography using CH2Cl2 and hexane to obtain Intermediate 7-c (0.5 g, 1.3 mmol, 59%).
The obtained compound was identified by ESI-LCMS as Intermediate 7-c. (ESI-LCMS: [M]+: C22H15N3O4. 385.11)
In an argon atmosphere, Intermediate 7-c (0.15 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 mixture was stirred at room temperature for 35 minutes and then concentrated under reduced pressure.
The obtained solid was separated and purified by column chromatography using CH2Cl2 and hexane to obtain Compound 7 (0.12 g, 0.27 mmol, 60%).
The obtained compound was identified by ESI-LCMS as Compound 7. (ESI-LCMS: [M]+: C25H15N5O3. 433.12)
In an argon atmosphere, 4-methyl-4H-benzo[4,5]selenopheno[3,2-b]selenopheno[2,3-d]pyrrole (13.6 mL, 40 mmol) was dissolved in 40 mL of THF, and the resultant mixture was cooled to −78° C. n-BuLi (27.5 mL, 1.6M in hexanes, 44 mmol) was added dropwise thereto for 10 minutes, and the mixture was stirred for 40 minutes. Then, the mixture was added dropwise to 20 mL of a THF solution of B(O-i-Pr)3 (13.9 mL, 60 mmol), which had been cooled to 0° C., for 15 minutes. The mixture was stirred at the same temperature for 1 hour and then at room temperature for 17 hours. After completion of the reaction, the solvent was removed therefrom under reduced pressure, and the reaction product was separated and purified by column chromatography using ethyl acetate and hexane to obtain Intermediate 9-a (7.6 g, 66
The obtained compound was identified by ESI-LCMS as Intermediate 9-a. (ESI-LCMS: [M]+: C13H10BNO2Se2. 382.91)
In an argon atmosphere, 4 mL of an ethanol (EtOH) solution of Intermediate 9-a (3.1 g, 8.0 mmol) and 3.6 mL of a 2M aqueous sodium carbonate (Na2CO3) solution were added to 10 mL of a toluene solution of 4-iodobenzo[c][1,2,5]selenadiazole (1.2 g, 4.0 mmol), and the resultant mixture was purged with nitrogen while being degassed. Then, Pd(PPh3)4 (0.3 g, 0.3 mmol) was added thereto, and the mixture was stirred at 80° C. for 12 hours. After cooling, an extraction process was performed thereon using water (500 mL) and ethyl acetate (300 mL) to collect an organic layer, which was then dried using anhydrous MgSO4 and filtered. The filtered solution was placed under reduced pressure to remove the solvent therefrom, and the obtained solid was separated and purified by column chromatography using CH2Cl2 and hexane to obtain Intermediate 9-b (1.3 g, 2.5 mmol, 61%).
The obtained compound was identified by ESI-LCMS as Intermediate 9-b. (ESI-LCMS: [M]+: C19H11N3Se3. 520.84)
In an argon atmosphere, Intermediate 9-b (1.2 g, 2.3 mmol) was dissolved in 50 mL of THF, and the resultant mixture was cooled to −78° C. n-BuLi (1.9 mL, 1.6M in hexanes, 3.0 mmol) was added thereto, and the mixture was stirred for 30 minutes. Then, DMF (0.2 mL, 3.0 mmol) was added thereto, and the mixture was stirred at the same temperature for 30 minutes and then at room temperature for 10 hours. After cooling, an extraction process was performed thereon using water (500 mL) and ethyl acetate (300 mL) to collect an organic layer, which was then dried using anhydrous MgSO4 and filtered. The filtered solution was placed under reduced pressure to remove the solvent therefrom, and the obtained solid was separated and purified by column chromatography using CH2Cl2 and hexane to obtain Intermediate 9-c (0.7 g, 1.3 mmol, 59%).
The obtained compound was identified by ESI-LCMS as Intermediate 9-c. (ESI-LCMS: [M]+: C20H11N3OSe3. 548.84)
In an argon atmosphere, Intermediate 9-c (0.22 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 mixture was stirred at room temperature for 35 minutes and then concentrated under reduced pressure. The obtained solid was separated and purified by column chromatography using CH2Cl2 and hexane to obtain Compound 9 (0.16 g, 0.27 mmol, 60%).
The obtained compound was identified by ESI-LCMS as Compound 9. (ESI-LCMS: [M]+: C23H11N5Se3. 596.85)
In an argon atmosphere, 4-butyl-4H-benzo[4,5]thieno[3,2-b]thieno[2,3-d]pyrrole (11.4 mL, 40 mmol) was dissolved in 40 mL of THF, and the resultant mixture was cooled to −78° C. n-BuLi (27.5 mL, 1.6M in hexanes, 44 mmol) was added dropwise thereto for 10 minutes, and the mixture was stirred for 40 minutes. Then, the mixture was added dropwise to 20 mL of a THF solution of B(O-i-Pr)3 (13.9 mL, 60 mmol), which had been cooled to 0° C., for 15 minutes. The mixture was stirred at the same temperature for 1 hour and then at room temperature for 17 hours. After completion of the reaction, the solvent was removed therefrom under reduced pressure, and the reaction product was separated and purified by column chromatography using ethyl acetate and hexane to obtain Intermediate 16-a (6.6 g, 65
The obtained compound was identified by ESI-LCMS as Intermediate 16-a. (ESI-LCMS: [M]+: C16H16BNO2S2. 329.07)
In an argon atmosphere, 4 mL of an ethanol (EtOH) solution of Intermediate 16-a (2.6 g, 8.0 mmol) and 3.6 mL of a 2M aqueous sodium carbonate (Na2CO3) solution were added to 10 mL of a toluene solution of 4-iodobenzo[c][1,2,5]selenadiazole (1.2 g, 4.0 mmol), and the resultant mixture was purged with nitrogen while being degassed. Then, Pd(PPh3)4 (0.3 g, 0.3 mmol) was added thereto, and the mixture was stirred at 80° C. for 12 hours. After cooling, an extraction process was performed thereon using water (500 mL) and ethyl acetate (300 mL) to collect an organic layer, which was then dried using anhydrous MgSO4 and filtered. The filtered solution was placed under reduced pressure to remove the solvent therefrom, and the obtained solid was separated and purified by column chromatography using CH2Cl2 and hexane to obtain Intermediate 16-b (1.2 g, 2.5 mmol, 63%).
The obtained compound was identified by ESI-LCMS as Intermediate 16-b. (ESI-LCMS: [M]+: C22H17N3S2Se. 467.00)
In an argon atmosphere, Intermediate 16-b (1.1 g, 2.3 mmol) was dissolved in 50 mL of THF, and the resultant mixture was cooled to −78° C. n-BuLi (1.9 mL, 1.6M in hexanes, 3.0 mmol) was added thereto, and the mixture was stirred for 30 minutes. Then, DMF (0.2 mL, 3.0 mmol) was added thereto, and the mixture was stirred at the same temperature for 30 minutes and then at room temperature for 10 hours. After cooling, an extraction process was performed thereon using water (500 mL) and ethyl acetate (300 mL) to collect an organic layer, which was then dried using anhydrous MgSO4 and filtered. The filtered solution was placed under reduced pressure to remove the solvent therefrom, and the obtained solid was separated and purified by column chromatography using CH2Cl2 and hexane to obtain Intermediate 16-c (0.6 g, 1.3 mmol, 57%).
The obtained compound was identified by ESI-LCMS as Intermediate 16-. (ESI-LCMS: [M]+: C23H17N3OS2Se. 495.00)
In an argon atmosphere, Intermediate 16-c (0.20 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 mixture was stirred at room temperature for 35 minutes and then concentrated under reduced pressure. The obtained solid was separated and purified by column chromatography using CH2Cl2 and hexane to obtain Compound 16 (0.15 g, 0.27 mmol, 59%).
The obtained compound was identified by ESI-LCMS as Compound 16. (ESI-LCMS: [M]+: C26H17N5S2Se. 543.01)
In an argon atmosphere, 4-butyl-4H-benzo[4,5]thieno[3,2-b]thieno[2,3-d]pyrrole (11.4 mL, 40 mmol) was dissolved in 40 mL of THF, and the mixture was cooled to −78° C. n-BuLi (27.5 mL, 1.6M in hexanes, 44 mmol) was added dropwise thereto for 10 minutes, and the resultant mixture was stirred for 40 minutes. Then, the mixture was added dropwise to 20 mL of a THF solution of B(O-i-Pr)3 (13.9 mL, 60 mmol), which had been cooled to 0° C., for 15 minutes. The mixture was stirred at the same temperature for 1 hour and then at room temperature for 17 hours. After completion of the reaction, the solvent was removed therefrom under reduced pressure, and the reaction product was separated and purified by column chromatography using ethyl acetate and hexane to obtain Intermediate 20-a (8.5 g, 65
The obtained compound was identified by ESI-LCMS as Intermediate 20-a. (ESI-LCMS: [M]+: C16H16BNO2Se2. 424.96)
In an argon atmosphere, 4 mL of an ethanol (EtOH) solution of Intermediate 20-a (3.4 g, 8.0 mmol) and 3.6 mL of a 2M aqueous sodium carbonate (Na2CO3) solution were added to 10 mL of a toluene solution of 4-iodobenzo[c][1,2,5]oxadiazole (1.0 g, 4.0 mmol), and the resultant mixture was purged with nitrogen while being degassed. Then, Pd(PPh3)4 (0.3 g, 0.3 mmol) was added thereto, and the mixture was stirred at 80° C. for 12 hours. After cooling, an extraction process was performed thereon using water (500 mL) and ethyl acetate (300 mL) to collect an organic layer, which was then dried using anhydrous MgSO4 and filtered. The filtered solution was placed under reduced pressure to remove the solvent therefrom, and the obtained solid was separated and purified by column chromatography using CH2Cl2 and hexane to obtain Intermediate 20-b (1.2 g, 2.5 mmol, 60%).
The obtained compound was identified by ESI-LCMS as Intermediate 20-b. (ESI-LCMS: [M]+: C22H17N3OSe2. 498.97)
In an argon atmosphere, Intermediate 20-b (1.1 g, 2.2 mmol) was dissolved in 50 mL of THF, and the resultant mixture was cooled to −78° C. n-BuLi (1.9 mL, 1.6M in hexanes, 3.0 mmol) was added thereto, and the mixture was stirred for 30 minutes. Then, DMF (0.2 mL, 3.0 mmol) was added thereto, and the mixture was stirred at the same temperature for 30 minutes and then at room temperature for 10 hours. After cooling, an extraction process was performed thereon using water (500 mL) and ethyl acetate (300 mL) to collect an organic layer, which was then dried using anhydrous MgSO4 and filtered. The filtered solution was placed under reduced pressure to remove the solvent therefrom, and the obtained solid was separated and purified by column chromatography using CH2Cl2 and hexane to obtain Intermediate 20-c (0.7 g, 1.3 mmol, 60%).
The obtained compound was identified by ESI-LCMS as Intermediate 20-c. (ESI-LCMS: [M]+: C23H17N3O2Se2. 526.97)
In an argon atmosphere, Intermediate 20-c (0.21 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 mixture was stirred at room temperature for 35 minutes and then concentrated under reduced pressure. The obtained solid was separated and purified by column chromatography using CH2Cl2 and hexane to obtain Compound 20 (0.15 g, 0.27 mmol, 59%).
The obtained compound was identified by ESI-LCMS as Compound 20. (ESI-LCMS: [M]+: C26H17N5OSe2. 574.98)
As an anode, a glass substrate with 15 Ω/cm2 (1,200 Å) ITO (manufactured by Corning. Inc.,) formed thereon was cut to a size of 50 mm×50 mm×0.7 mm, and sonicated with isopropyl alcohol and pure water, each for 5 minutes. Then, ultraviolet light was irradiated for 30 minutes thereto, and ozone was exposed thereto for cleaning. Subsequently, the resultant glass substrate was 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 and having a thickness of 200 Å.
Fullerene was vacuum-deposited on the first layer to form a second layer included in the photoactive layer and 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 ET1 was vacuum-deposited on the hole blocking layer to form an electron transport layer having a thickness of 300 Å. Liq was vacuum-deposited on the electron transport layer to form an electron injection layer having a thickness of 10 Å. AgMg was vacuum-deposited on the electron injection layer to form a cathode having a thickness of 100 Å, thereby completing the manufacture of an opto-electronic device:
Opto-electronic devices were manufactured in substantially the same manner as in Comparative Example 1, except that, when forming a first layer included in a photoactive layer, the compounds shown in Table 1 were each used instead of SubPC.
To evaluate the characteristics of the compounds respectively used in the first layers in Examples 1 to 5 and Comparative Examples 1 to 5, the highest occupied molecular orbital (HOMO) energy level, LUMO energy level, maximum absorption wavelength (λabs), oscillator strength (OSC), exciton binding energy (Eb) and molecular weight (MW) of each compound were measured, and the results are shown in Table 1.
In evaluating the above characteristics, the HOMO and LUMO energy levels and oscillator strength in a structurally optimized state and an excited state were evaluated by performing quantum simulation at a level of B3LYP/6-311 G** based on the time-dependent density functional theory (TD-DFT) method by using the Gaussian program.
Compound A
Compound B
Compound C
Evaluation Example 2
To evaluate the characteristics of the opto-electronic devices manufactured in Examples 1 to 5 and Comparative Examples 1 to 5, the external quantum efficiency (EQE) and dark current density (Jdark) of each opto-electronic device were measured, and the results are shown in Table 2.
In measuring the external quantum efficiency (EQE), each of the opto-electronic devices manufactured in Examples 1 to 5 and Comparative Examples 1 to 5 was irradiated with light (wavelength of 630 nm) by using an external quantum efficiency meter (K3100, McScience, Korea), a generated current value was measured by using 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 using an ammeter (Keithley, Tektronix, USA) in a state in which a voltage was applied to an anode at a dark current density with a reverse bias of −3 V by using electro-optical characteristics evaluation equipment (K3100, McScience, Korea).
Referring to Table 1, the opto-electronic devices according to Examples 1 to 5, which had a maximum absorption wavelength coinciding with the center of a red wavelength, showed improved light absorption efficiency compared to the opto-electronic devices according to Comparative Examples 1 to 5, which had a maximum absorption wavelength deviating from the center of a red wavelength. Referring to Table 2, the opto-electronic devices according to Examples 1 to 5 have high external quantum efficiency (EQE) and low dark current density (Jdark) compared to the opto-electronic devices according to Comparative Examples 1 to 5. Accordingly, the opto-electronic devices according to Examples 1 to 5 have excellent opto-electronic characteristics.
According to the one or more embodiments, an organic compound represented by Formula 1 may have excellent light absorption efficiency for a set or specific wavelength. Accordingly, an opto-electronic device including the organic compound may have high light absorption efficiency. An electronic apparatus including the opto-electronic device and an electronic device using the electronic apparatus may have improved quality.
It should be understood that embodiments described herein should be considered in a descriptive sense only and not for purposes of limitation. Descriptions of features or aspects within each embodiment should typically be considered as available for other similar features or aspects in other embodiments. While one or more embodiments have been described with reference to the figures, it will be understood by those of ordinary skill in the art that various changes in form and details may be made therein without departing from the spirit and scope as defined by the claims, and equivalents thereof.
| Number | Date | Country | Kind |
|---|---|---|---|
| 10-2022-0148133 | Nov 2022 | KR | national |
