Patent Application
20230180605
This application claims priority to and the benefit of Korean Patent Application No. 10-2021-0174013, filed on Dec. 7, 2021, in the Korean Intellectual Property Office, the entire content of which is hereby incorporated by reference.
One or more embodiments of the present disclosure relate to an organic photodetector and an electronic apparatus including the same.
Photoelectric devices are devices that convert light and an electrical signal and include a photodiode and a phototransistor. Photoelectric devices may be applied to an image sensor, a solar cell, an organic light-emitting device, and/or the like.
In the case of silicon, which is mainly used in photodiodes, as the size of pixels decreases, an absorption region may decrease, thereby deteriorating or reducing sensitivity. Accordingly, organic materials that may replace silicon are being studied.
As organic materials have a large extinction coefficient and may selectively absorb light in a set or specific wavelength region according to the molecular structure thereof, organic materials may replace photodiodes and color filters concurrently (e.g., simultaneously), which may facilitate improvements in sensitivity and high integration.
An organic photodetector (OPD) including such an organic material may be applied to, for example, a display apparatus and/or an image sensor.
Provided are an organic photodetector and an electronic apparatus including the same, the organic photodetector including an activation layer material having superior processability, mass production, and efficiency compared to those of a fullerene.
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 present disclosure.
According to one or more embodiments,
an organic photodetector includes a first electrode,
a second electrode facing the first electrode, and
an activation layer between the first electrode and the second electrode,
wherein the activation layer includes a compound represented by Formula 1 below:
In Formula 1, R1 to R6 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono 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-C10 cycloalkyl group unsubstituted or substituted with at least one R10a, a C1-C10 heterocycloalkyl group unsubstituted or substituted with at least one R10a, a C3-C10 cycloalkenyl group unsubstituted or substituted with at least one R10a, a C1-C10 heterocycloalkenyl group unsubstituted or substituted with at least one R10a, a C6-C60 aryl 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 C1-C60 heteroaryl group unsubstituted or substituted with at least one R10a, a C1-C60 heteroaryloxy group unsubstituted or substituted with at least one R10a, a C1-C60 heteroarylthio group unsubstituted or substituted with at least one R10a, a monovalent non-aromatic condensed polycyclic group unsubstituted or substituted with at least one R10a, a monovalent non-aromatic condensed heteropolycyclic group unsubstituted or substituted with at least one R10a, —Si(Q1)(Q2)(Q3), —B(Q1)(Q2), —N(Q1)(Q2), —P(Q1)(Q2), —C(═O)(Q1), —S(═O)(Q1), —S(═O)2(Q1), —P(═O)(Q1)(Q2), or —P(═S)(Q1)(Q2),
an octyl group and a tridecyl group may be excluded from R1 and R2,
a3 to a6 may each independently be an integer of 1 or 2,
R10a may be:
deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group,
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 arylalkyl group, a C2-C60 heteroarylalkyl group, —Si(Q11)(Q12)(Q13), —N(Q11)(Q12), —B(Q11)(Q12), —C(═O)(Q11), —S(═O)2(Q11), —P(═O)(Q11)(Q12), or any combination thereof,
a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 arylalkyl group, or a C2-C60 heteroarylalkyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 arylalkyl group, a C2-C60 heteroarylalkyl group, —Si(Q21)(Q22)(Q23), —N(Q21)(Q22), —B(Q21)(Q22), —C(═O)(Q21), —S(═O)2(Q21), —P(═O)(Q21)(Q22), or any combination thereof, or
—Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), or —P(═O)(Q31)(Q32), and
Q1 to Q3, Q11 to Q13, Q21 to Q23, and Q31 to Q33 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, or a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C7-C60 arylalkyl group, or a C2-C60 heteroarylalkyl group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof.
In an embodiment, in Formula 1, R1 and R2 may each independently be a C1-C60 alkyl group that is unsubstituted or substituted with at least one R10a, and R3 to R6 may each independently be a C6-C60 aryl group that is unsubstituted or substituted with at least one R10a or a C1-C60 heteroaryl group that is unsubstituted or substituted with at least one R10a.
In an embodiment, the activation layer may include the compound represented by Formula 1 as an electron acceptor or an electron donor.
In an embodiment, the activation layer may include the compound represented by Formula 1 and an electron donor.
In an embodiment, the activation layer may include a layer including the compound represented by Formula 1, and a layer including an electron donor.
In an embodiment, the layer including the compound represented by Formula 1 and the layer including the electron donor may be in contact (e.g., physical contact) with each other.
In an embodiment, the activation layer may include a layer including a mixture of the compound represented by Formula 1 and an electron donor.
In an embodiment, the activation layer may include a layer consisting of the compound represented by Formula 1.
In an embodiment, the activation layer may include a layer including an electron donor, a layer including a mixture of the compound represented by Formula 1 and an electron donor, and a layer consisting of the compound represented by Formula 1.
In an embodiment, the layer including the electron donor and the layer including the mixture of the compound represented by Formula 1 and the electron donor may be in contact (e.g., physical contact) with each other, and
the layer including the mixture of the compound represented by Formula 1 and the electron donor and the layer consisting of the compound represented by Formula 1 may be in contact (e.g., physical contact) with each other.
In an embodiment, the activation layer may include a layer including a mixture of a hole transporting material and the compound represented by Formula 1.
In an embodiment, the activation layer may include a p-dopant.
In an embodiment, the first electrode may be an anode,
the second electrode may be a cathode,
the organic photodetector may further include a hole transport region between the activation layer and the first electrode, and
the hole transport region may include a hole injection layer, a hole transport layer, an auxiliary layer, an electron blocking layer, or any combination thereof.
In an embodiment, the first electrode may be an anode,
the second electrode may be a cathode,
the organic photodetector may further include an electron transport region between the activation layer and the second electrode, and
the electron transport region may include a buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.
According to one or more embodiments, an electronic apparatus includes the organic photodetector.
In an embodiment, the electronic apparatus may further include a light-emitting device.
According to one or more embodiments,
an electronic apparatus includes a substrate including a light detection region and an emission region,
an organic photodetector on the light detection region, and
a light-emitting device on the emission region,
wherein the organic photodetector includes a first pixel electrode, a counter electrode facing the first pixel electrode, and a hole transport region, an activation layer, and an electron transport region, which are sequentially between the first pixel electrode and the counter electrode,
the light-emitting device includes a second pixel electrode, the counter electrode facing the second pixel electrode, and the hole transport region, an emission layer, and the electron transport region, which are sequentially between the second pixel electrode and the counter electrode,
the first pixel electrode and the activation layer are arranged in correspondence with the light detection region,
the second pixel electrode and the emission layer are arranged in correspondence with the emission region,
the hole transport region, the electron transport region, and the counter electrode are arranged throughout the light detection region and the emission region, and
the activation layer includes the compound represented by Formula 1
In Formula 1, R1 to R6 and a3 to a6 are respectively the same as described above.
The hole transport region and the electron transport region are respectively the same as described below.
The above and other aspects and features of certain embodiments of the present 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 the specification. 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, 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 present disclosure, the expression “at least one of a, b or 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.
The subject matter of the present disclosure may include various modifications and various embodiments, and example embodiments will be illustrated in the drawings and described in more detail in the detailed description. Effects and features of embodiments of the present disclosure, and implementation methods therefor will become clear with reference to the embodiments described herein below together with the drawings. The subject matter of the present disclosure may, however, be embodied in many different forms and should not be construed as limited to the embodiments set forth herein.
As used herein, the singular forms “a,” “an” and “the” are intended to include the plural forms as well, unless the context clearly indicates otherwise.
As used herein, the terms “comprise”, “include”, “have”, and the like, specify the presence of stated features and/or components, and do not exclude the presence of addition of one or more other features and/or components.
It will be understood that when a layer, region, or component is referred to as being “on” or “onto” another layer, region, or component, it may be directly or indirectly formed over the other layer, region, or component. For example, intervening layers, regions, or components may be present.
Like reference numerals in the drawings denote like elements, and thus duplicative description thereof may not be repeated.
Sizes of components in the drawings may be exaggerated for convenience of explanation. In other words, the sizes and thicknesses of elements may be arbitrarily illustrated in the drawings for the convenience of explanation, and the present disclosure is not limited thereto.
Referring to
In
In the related art, the activation layer 140 includes a fullerene (C60) as a representative electron acceptor material.
However, fullerenes require a high deposition temperature of 500° C. or higher and special additional measures due to characteristics of popping up (e.g., exploding) when heated during processing (e.g., deposition). Also, because the price of fullerenes is high, the unit price of a final product is eventually increased.
In an embodiment, the activation layer 140 may include a compound represented by Formula 1 below:
wherein, in Formula 1, R1 to R6 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono 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-C10 cycloalkyl group unsubstituted or substituted with at least one R10a, a C1-C10 heterocycloalkyl group unsubstituted or substituted with at least one R10a, a C3-C10 cycloalkenyl group unsubstituted or substituted with at least one R10a, a C1-C10 heterocycloalkenyl group unsubstituted or substituted with at least one R10a, a C6-C60 aryl 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 C1-C60 heteroaryl group unsubstituted or substituted with at least one R10a, a C1-C60 heteroaryloxy group unsubstituted or substituted with at least one R10a, a C1-C60 heteroarylthio group unsubstituted or substituted with at least one R10a, a monovalent non-aromatic condensed polycyclic group unsubstituted or substituted with at least one R10a, a monovalent non-aromatic condensed heteropolycyclic group unsubstituted or substituted with at least one R10a, —Si(Q1)(Q2)(Q3), —B(Q1)(Q2), —N(Q1)(Q2), —P(Q1)(Q2), —C(═O)(Q1), —S(═O)(Q1), —S(═O)2(Q1), —P(═O)(Q1)(Q2), or —P(═S)(Q1)(Q2),
an octyl group and a tridecyl group may be excluded from R1 and R2,
a3 to a6 may each independently be an integer of 1 or 2,
R10a may be:
deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 arylalkyl group, a C2-C60 heteroarylalkyl group, —Si(Q11)(Q12)(Q13), —N(Q11)(Q12), —B(Q11)(Q12), —C(═O)(Q11), —S(═O)2(Q11), —P(═O)(Q11)(Q12), or any combination thereof;
a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 arylalkyl group, or a C2-C60 heteroarylalkyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 arylalkyl group, a C2-C60 heteroarylalkyl group, —Si(Q21)(Q22)(Q23), —N(Q21)(Q22), —B(Q21)(Q22), —C(═O)(Q21), —S(═O)2(Q21), —P(═O)(Q21)(Q22), or any combination thereof; or
—Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), or —P(═O)(Q31)(Q32), and
Q1 to Q3, Q11 to Q13, Q21 to Q23, and Q31 to Q33 may each independently be: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; a C1-C60 alkyl group; a C2-C60 alkenyl group; a C2-C60 alkynyl group; a C1-C60 alkoxy group; or a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C7-C60 arylalkyl group, or a C2-C60 heteroarylalkyl group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof.
In an embodiment, in Formula 1, R1 and R2 may each independently be a C1-C60 alkyl group that is unsubstituted or substituted with at least one R10a, and
R3 to R6 may each independently be a C6-C60 aryl group that is unsubstituted or substituted with at least one R10a or a C1-C60 heteroaryl group that is unsubstituted or substituted with at least one R10a.
In an embodiment, R3 to R6 may each independently be 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, 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, or a naphthyridinyl group, each unsubstituted or substituted with at least one R10a.
In an embodiment, the compound represented by Formula 1 may be one selected from the following compounds:
The compound represented by Formula 1 according to an embodiment of the present disclosure does not have special problems during processing and is not expensive, as compared to fullerenes. In an embodiment, it has been confirmed that efficiency of an organic photodetector using the compound represented by Formula 1 has shown an excellent result as compared to fullerenes.
The activation layer 140 generates excitons by receiving light from the outside (e.g., external light) and divides the generated excitons into holes and electrons. The activation layer 140 may include an electron donor and an electron acceptor.
In an embodiment, the activation layer 140 may include the compound represented by Formula 1 as an electron acceptor or an electron donor.
The compound represented by Formula 1 may act as an electron acceptor or an electron donor. In an embodiment, the activation layer 140 may include: the compound represented by Formula 1; and an electron donor or an electron acceptor.
In an embodiment, the activation layer 140 may include: a layer including the compound represented by Formula 1; and a layer including an electron donor or an electron acceptor. In this case, the compound represented by Formula 1 may act as the electron acceptor or the electron donor.
In an embodiment, the layer including the compound represented by Formula 1 and the layer including the electron donor or the electron acceptor may be in contact with each other. The layer including the compound represented by Formula 1 and the layer including the electron donor or the electron acceptor may physically be in direct contact with each other (e.g., direct physical contact with each other with no intervening layers or components therebetween).
In an embodiment, the layer including the compound represented by Formula 1 and the layer including the electron donor or the electron acceptor may form a PN junction. Excitons may be efficiently separated into holes and electrons by photo-induced charge separation occurring at an interface between these layers. Furthermore, because the activation layer 140 is separated into the layer including the compound represented by Formula 1 and the layer including the electron donor, holes and electrons generated at the interface may be easily trapped or may easily migrate.
In an embodiment, the activation layer 140 may include a layer including a mixture of the compound represented by Formula 1 and an electron donor or an electron acceptor. In this case, the compound represented by Formula 1 may act as the electron acceptor or the electron donor. In this case, the activation layer 140 may be formed by co-depositing the compound represented by Formula 1 and the electron donor or the electron acceptor. When the activation layer 140 is a mixed layer, excitons may be generated with a diffusion distance from a donor-acceptor interface, and thus, the organic photodetector may have improved external quantum efficiency. A ratio of the compound represented by Formula 1 and the electron donor or the electron acceptor may be, for example, in a range of 10:90 to 90:10 (weight ratio).
In an embodiment, the activation layer 140 may include a layer consisting of the compound represented by Formula 1. In this case, the compound represented by Formula 1 may act as an electron acceptor, an electron transport material, and/or an electron donor.
In an embodiment, the activation layer may include:
a layer including an electron donor or an electron acceptor;
a layer including a mixture of the compound represented by Formula 1 and an electron donor or an electron acceptor; and
a layer consisting of the compound represented by Formula 1.
In this case, the compound represented by Formula 1 may act as the electron acceptor or the electron donor. In the layer including the mixture of the compound represented by Formula 1 and the electron donor or the electron acceptor, a ratio of the compound represented by Formula 1 and the electron donor or the electron acceptor may be in a range of, for example, 10:90 to 90:10 (weight ratio).
In an embodiment,
the layer including the electron donor or the electron acceptor and the layer including the mixture of the compound represented by Formula 1 and the electron donor or the electron acceptor may be in contact (e.g., physical contact) with each other, and
the layer including the mixture of the compound represented by Formula 1 and the electron donor or the electron acceptor and the layer consisting of the compound represented by Formula 1 may be in contact (e.g., physical contact) with each other.
In an embodiment, the layer including the electron donor or the electron acceptor and the layer including the mixture of the compound represented by Formula 1 and the electron donor or the electron acceptor may physically be in direct contact with each other (e.g., may be in direct physical contact with no other layers or components therebetween), and
the layer including the mixture of the compound represented by Formula 1 and the electron donor or the electron acceptor and the layer consisting of the compound represented by Formula 1 may physically be in direct contact with each other (e.g., may be in direct physical contact with no other layers or components therebetween).
In an embodiment, the activation layer may include a layer including a mixture of a hole transporting material and the compound represented by Formula 1. The hole transporting material will be further described herein below. A ratio of the hole transporting material and the compound represented by Formula 1 may be in a range of, for example, 10:90 to 90:10 (weight ratio).
In an embodiment, the activation layer 140 may include a p-dopant. The p-dopant may be homogeneously or non-homogeneously dispersed in the activation layer 140. The activation layer 140 is doped with the p-dopant, and thus, external quantum efficiency may be improved by the charge injection principle by an electric field. The p-dopant will be further described herein below.
In an embodiment, the electron donor may be an organic or inorganic material having a lowest unoccupied molecular orbital (LUMO) energy level deeper than about −2 eV and a highest occupied molecular orbital (HOMO) energy level deeper than about −3 eV. In an embodiment, the electron donor may be an organic and/or inorganic material having a LUMO energy level of about −3 eV to about −5 eV and a HOMO energy level of about −4 eV to about −7 eV. In an embodiment, the electron donor may be boron subphthalocyanine chloride (SubPc), copper(II) phthalocyanine (CuPc), tetraphenyldibenzoperiflanthene (DBP), or any combination thereof.
In an embodiment, the electron acceptor may be an organic and/or inorganic material having a LUMO energy level deeper than about −3 eV and a HOMO energy level deeper than about −4 eV. In an embodiment, the electron acceptor may be an organic or inorganic material having a LUMO energy level of about −4 eV to about −6 eV and a HOMO energy level of about −5 eV to about −8 eV. In an embodiment, the electron acceptor may be a C60 fullerene, HATCN, TCNQ, etc.
One selected from the first electrode 110 and the second electrode 170 may be an anode, and the other one may be a cathode. In an embodiment, the first electrode 110 may be an anode, and the second electrode 170 may be a cathode.
A hole transport region of the organic photodetector 10 may include a structure in which the hole injection layer 120, the hole transport layer 130, an auxiliary layer, an electron blocking layer, or any combination thereof are on the first electrode 110. In an embodiment, the auxiliary layer may be between the hole transport layer 130 and the activation layer 140.
An electron transport region of the organic photodetector 10 may include a structure in which a buffer layer, a hole blocking layer, the electron transport layer 150, the electron injection layer 160, or any combination thereof are on the activation layer 140. In an embodiment, the buffer layer may be between the electron transport layer 150 and the activation layer 140.
In an embodiment, the p-dopant may include a quinone derivative, a cyano group-containing compound, a compound including element EL1 and element EL2, or any combination thereof.
Examples of the quinone derivative may include TCNQ, F4-TCNQ, etc.
Examples of the cyano group-containing compound may include HAT-CN, a compound represented by Formula 221 below, etc.:
wherein, in Formula 221,
R221 to R223 may each independently be a C3-C60 carbocyclic group that is unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group that is 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 that is substituted with a cyano group, —F, —Cl, —Br, —I, or any combination thereof; or any combination thereof.
In the compound including element EL1 and element EL2, element EL1 may be metal, metalloid, or a combination thereof, and element EL2 may be non-metal, metalloid, or a combination thereof.
Examples of the metal may include an alkali metal (for example, lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), etc.); an alkaline earth metal (for example, beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), etc.); a transition metal (for example, titanium (Ti), zirconium (Zr), hafnium (Hf), vanadium (V), niobium (Nb), tantalum (Ta), chromium (Cr), molybdenum (Mo), tungsten (W), manganese (Mn), technetium (Tc), rhenium (Re), iron (Fe), ruthenium (Ru), osmium (Os), cobalt (Co), rhodium (Rh), iridium (Ir), nickel (Ni), palladium (Pd), platinum (Pt), copper (Cu), silver (Ag), gold (Au), etc.); a post-transition metal (for example, zinc (Zn), indium (In), tin (Sn), etc.); and a lanthanide metal (for example, lanthanum (La), cerium (Ce), praseodymium (Pr), neodymium (Nd), promethium (Pm), samarium (Sm), europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb), lutetium (Lu), etc.).
Examples of the metalloid may include silicon (Si), antimony (Sb), and tellurium (Te).
Examples of the non-metal may include oxygen (O) and halogen (for example, F, Cl, Br, I, etc.).
In an embodiment, examples of the compound containing element EL1 and element EL2 may include metal oxide, metal halide (for example, metal fluoride, metal chloride, metal bromide, and/or metal iodide), metalloid halide (for example, metalloid fluoride, metalloid chloride, metalloid bromide, and/or metalloid iodide), metal telluride, or any combination thereof.
Examples of the metal oxide may include tungsten oxide (for example, WO, W2O3, WO2, WO3, W2O5, etc.), vanadium oxide (for example, VO, V2O3, VO2, V2O5, etc.), molybdenum oxide (MoO, Mo2O3, MoO2, MoO3, Mo2O5, etc.), and rhenium oxide (for example, ReO3, etc.).
Examples of the metal halide may include alkali metal halide, alkaline earth metal halide, transition metal halide, post-transition metal halide, and lanthanide metal halide.
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, and CsI.
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, and BaI2.
Examples of the transition metal halide may include titanium halide (for example, TiF4, TiCl4, TiBr4, TiI4, etc.), zirconium halide (for example, ZrF4, ZrCl4, ZrBr4, ZrI4, etc.), hafnium halide (for example, HfF4, HfCl4, HfBr4, HfI4, etc.), vanadium halide (for example, VF3, VCl3, VBr3, VI3, etc.), niobium halide (for example, NbF3, NbCl3, NbBr3, NbI3, etc.), tantalum halide (for example, TaF3, TaCl3, TaBr3, TaI3, etc.), chromium halide (for example, CrF3, CrCl3, CrBr3, CrI3, etc.), molybdenum halide (for example, MoF3, MoCl3, MoBr3, MoI3, etc.), tungsten halide (for example, WF3, WCl3, WBr3, WI3, etc.), manganese halide (for example, MnF2, MnCl2, MnBr2, MnI2, etc.), technetium halide (for example, TcF2, TcCl2, TcBr2, TcI2, etc.), rhenium halide (for example, ReF2, ReCl2, ReBr2, ReI2, etc.), iron halide (for example, FeF2, FeCl2, FeBr2, FeI2, etc.), ruthenium halide (for example, RuF2, RuCl2, RuBr2, RuI2, etc.), osmium halide (for example, OsF2, OsCl2, OsBr2, OsI2, etc.), cobalt halide (for example, CoF2, CoCl2, CoBr2, CoI2, etc.), rhodium halide (for example, RhF2, RhCl2, RhBr2, RhI2, etc.), iridium halide (for example, IrF2, IrCl2, IrBr2, IrI2, etc.), nickel halide (for example, NiF2, NiCl2, NiBr2, NiI2, etc.), palladium halide (for example, PdF2, PdCl2, PdBr2, PdI2, etc.), platinum halide (for example, PtF2, PtCl2, PtBr2, PtI2, etc.), copper halide (for example, CuF, CuCl, CuBr, CuI, etc.), silver halide (for example, AgF, AgCl, AgBr, AgI, etc.), and gold halide (for example, AuF, AuCl, AuBr, AuI, etc.).
Examples of the post-transition metal halide may include zinc halide (for example, ZnF2, ZnCl2, ZnBr2, ZnI2, etc.), indium halide (for example, InI3, etc.), and tin halide (for example, SnI2, etc.).
Examples of the lanthanide metal halide may include YbF, YbF2, YbF3, SmF3, YbCl, YbCl2, YbCl3 SmCl3, YbBr, YbBr2, YbBr3, SmBr3, YbI, YbI2, YbI3, and SmI3.
Examples of the metalloid halide may include antimony halide (for example, SbCl5, etc.).
Examples of the metal telluride may include alkali metal telluride (for example, Li2Te, Na2Te, K2Te, Rb2Te, Cs2Te, etc.), alkaline earth metal telluride (for example, BeTe, MgTe, CaTe, SrTe, BaTe, etc.), transition metal telluride (for example, TiTe2, ZrTe2, HfTe2, V2Te3, Nb2Te3, Ta2Te3, Cr2Te3, Mo2Te3, W2Te3, MnTe, TcTe, ReTe, FeTe, RuTe, OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, Cu2Te, CuTe, Ag2Te, AgTe, Au2Te, etc.), post-transition metal telluride (for example, ZnTe, etc.), and lanthanide metal telluride (for example, LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, etc.).
In an embodiment, an amount of the p-dopant in the activation layer 140 may be in a range of about 0.1 vol % to about 10 vol %, for example, about 0.5 vol % to about 5 vol %.
The activation layer 140 may have a thickness of about 200 Å to about 2,000 Å, for example, about 400 Å to about 600 Å.
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, the material for forming the first electrode 110 may be a high-work function material.
The first electrode 110 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. To form the first electrode 110 as a transmissive electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or any combination thereof may be used as the material for forming the first electrode 110. In an embodiment, to form the first electrode 110 as a semi-transmissive electrode or a reflective electrode, magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), or any combination thereof may be used as the material for forming the first electrode 110.
The first electrode 110 may have a single-layered structure consisting of a single layer or a multilayer structure including a plurality of layers. In an embodiment, the first electrode 110 may have a three-layered structure of ITO/Ag/ITO.
The organic photodetector 10 according to an embodiment may include a charge auxiliary layer that facilitates migration of holes and electrons from the activation layer 140.
The charge auxiliary layer may include the hole injection layer 120 and the hole transport layer 130, which facilitate migration of holes, and may include the electron transport layer 150 and the electron injection layer 160, which facilitate migration of electrons.
Charge auxiliary layers between the first electrode 110 and the activation layer 140 may be collectively referred to as a hole transport region.
The hole transport region may include the hole injection layer 120, the hole transport layer 130, the auxiliary layer, and the electron blocking layer.
The hole transport region may include a hole transporting material. In an embodiment, the hole transporting material may include a compound represented by Formula 201 below, a compound represented by Formula 202 below, or any combination thereof:
wherein, in Formulae 201 and 202,
L201 to L204 may each independently be a C3-C60 carbocyclic group that is unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group that is 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 that is unsubstituted or substituted with at least one R10a, or a C1-C60 heterocyclic group that is 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 that is unsubstituted or substituted with at least one R10a, or a C2-C5 alkenylene group that is unsubstituted or substituted with at least one R10a to form a C8-C60 polycyclic group (for example, a carbazole group and/or the like) that is unsubstituted or substituted with at least one R10a (for example, Compound HT16),
R203 and R204 may optionally be linked to each other via a single bond, a C1-C5 alkylene group that is unsubstituted or substituted with at least one R10a, or a C2-C5 alkenylene group that is unsubstituted or substituted with at least one R10a to form a C8-C60 polycyclic group that is unsubstituted or substituted with at least one R10a, and
na1 may be an integer from 1 to 4.
In an embodiment, 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 the same as described with respect to R10a, ring CY201 to ring CY204 may each independently be a C3-C20 carbocyclic group or a C1-C20 heterocyclic group, and at least one hydrogen in Formulae CY201 to CY217 may be unsubstituted or substituted with R10a as described above.
In an embodiment, 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 an embodiment, each of Formulae 201 and 202 may include at least one selected from groups represented by Formulae CY201 to CY203.
In an embodiment, 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 an embodiment, xa1 in Formula 201 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 an embodiment, each of Formulae 201 and 202 may not include groups represented by Formulae CY201 to CY203.
In an embodiment, each of Formulae 201 and 202 may not include groups represented by Formulae CY201 to CY203, and may include at least one selected from groups represented by Formulae CY204 to CY217.
In an embodiment, each of Formulae 201 and 202 may not include groups represented by Formulae CY201 to CY217.
In an embodiment, the hole transporting material may include one selected from Compounds HT1 to HT46, m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, Spiro-TPD, Spiro-NPB, methylated-NPB, TAPC, HMTPD, 4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphor sulfonic acid (PANI/CSA), polyaniline/poly(4-styrenesulfonate) (PANI/PSS), or any combination thereof:
A thickness of the hole transport region may be in a range of about 50 Å to about 10,000 Å, for example, about 100 Å to about 4,000 Å. When the hole transport region includes a hole injection layer, a hole transport layer, or any combination thereof, a thickness of the hole injection layer may be in a range of about 100 Å to about 9,000 Å, for example, about 100 Å to about 1,000 Å, and a thickness of the hole transport layer may be in a range of about 50 Å to about 2,000 Å, for example, about 100 Å to about 1,500 Å. When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, suitable or satisfactory hole-transporting characteristics may be obtained without a substantial increase in driving voltage.
The auxiliary layer may compensate for an optical resonance distance according to a wavelength of light introduced to the activation layer 140 to increase light introduction efficiency. Also, the auxiliary layer may lower an energy barrier of holes in a direction of the hole transport layer and the anode to facilitate migration of holes. The electron blocking layer may prevent or reduce leakage of electrons from the activation layer 140 into the hole transport region. The hole transporting material may be included in the auxiliary layer and the electron blocking layer.
The charge auxiliary layers between the activation layer 140 and the second electrode 170 may be collectively referred to as an electron transport region.
The electron transport region 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 electron transport region may include a buffer layer, a hole blocking layer, the electron transport layer 150, the electron injection layer 160, or any combination thereof.
In an embodiment, the electron transport region may have an electron transport layer/electron injection layer structure, a hole blocking layer/electron transport layer/electron injection layer structure, or a buffer layer/electron transport layer/electron injection layer structure, wherein the constituent layers of each structure are stacked sequentially from the activation layer 140.
The electron transport region (e.g., a buffer layer, a hole blocking layer, and/or an electron transport layer in the electron transport region) may include a metal-free compound including at least one 7 electron-deficient nitrogen-containing C1-C60 cyclic group.
In an embodiment, the electron transport region may include a compound represented by Formula 601 below:
[Ar601]xe11-[(L601)xe1-R601])xe21 Formula 601
wherein, in Formula 601,
Ar601 and L601 may each independently be a C3-C60 carbocyclic group that is unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group that is 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 C3-C60 carbocyclic group that is unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group that is 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 are respectively the same as described in connection with Q1 in the present specification,
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 that is unsubstituted or substituted with at least one R10a.
In an embodiment, when xe11 in Formula 601 is 2 or more, two or more of
Ar601(s) may be linked via a single bond.
In an embodiment, Ar601 in Formula 601 may be a substituted or unsubstituted anthracene group.
In an embodiment, the electron transport region 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), at least one selected from X614 to X616 may be N,
L611 to L613 are respectively the same as those described in connection with L601,
xe611 to xe613 are respectively the same as those described in connection with xe1
R611 to R613 are respectively the same as those described 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.
In an embodiment, xe1 and xe611 to xe613 in Formulae 601 and 601-1 may each independently be 0, 1, or 2.
The electron transport region may include 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, NTAZ, or any combination thereof:
A thickness of the hole transport region may be in a range of about 50 Å to about 5,000 Å, for example, about 100 Å to about 4,000 Å. When the electron transport region includes a buffer layer, a hole blocking layer, an electron transport layer, or any combination thereof, the thicknesses of the buffer layer and the hole blocking 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 the 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, and/or the electron transport layer are within any of these ranges, excellent electron-transporting characteristics may be obtained without a substantial increase in driving voltage.
The electron transport region (for example, the electron transport layer in the electron transport region) may further include, in addition to the materials described above, a metal-containing material.
The metal-containing material may include an alkali metal complex, an alkaline earth metal complex, or any combination thereof. A metal ion of the alkali metal complex may be a Li ion, a Na ion, a K ion, a Rb ion, or a Cs ion, and a metal ion of the alkaline earth metal complex may be a Be ion, a Mg ion, a Ca ion, a Sr ion, or a Ba ion. A ligand coordinated with the metal ion of the alkali metal complex or the alkaline earth-metal complex may include a hydroxyquinoline, a hydroxyisoquinoline, a hydroxybenzoquinoline, a hydroxyacridine, a hydroxyphenanthridine, a hydroxyphenyloxazole, a hydroxyphenylthiazole, a hydroxyphenyloxadiazole, a hydroxyphenylthiadiazole, a hydroxyphenylpyridine, a hydroxyphenylbenzimidazole, a hydroxyphenylbenzothiazole, a bipyridine, a phenanthroline, a cyclopentadiene, or any combination thereof.
In an embodiment, 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 may include an electron injection layer that facilitates electron injection. The electron injection layer may be in direct contact (e.g., physical contact) with the second electrode 170.
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 consisting of 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 (for example, fluorides, chlorides, bromides, and/or iodides), and/or tellurides of the alkali metal, the alkaline earth metal, and the rare earth metal, or any combination thereof.
The alkali metal-containing compound may include alkali metal oxides, such as Li2O, Cs2O, and/or K2O, alkali metal halides, 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, such as BaO, SrO, CaO, BaxSr1-xO (x is a real number satisfying the condition of 0<x<1), BaxCa1-xO (x is a real number satisfying the condition of 0<x<1), and/or the like. The rare earth metal-containing compound may include YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3, TbF3, YbI3, ScI3, TbI3, or any combination thereof. In an embodiment, 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, and Lu2Te3.
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 bonded to the metal ion, for example, a hydroxyquinoline, a hydroxyisoquinoline, a hydroxybenzoquinoline, a hydroxyacridine, a hydroxyphenanthridine, a hydroxyphenyloxazole, a hydroxyphenylthiazole, a hydroxyphenyloxadiazole, a hydroxyphenylthiadiazole, a hydroxyphenylpyridine, a hydroxyphenyl benzimidazole, a hydroxyphenylbenzothiazole, a bipyridine, a phenanthroline, a cyclopentadiene, or any combination thereof.
The electron injection layer may include (e.g., consist of) an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof, as described above. In an embodiment, the electron injection layer may further include an organic material (for example, a compound represented by Formula 601).
In an embodiment, the electron injection layer may include (e.g., consist of) i) an alkali metal-containing compound (for example, an alkali metal halide), ii) a) an alkali metal-containing compound (for example, an alkali metal halide); and b) an alkali metal, an alkaline earth metal, a rare earth metal, or any combination thereof. In an embodiment, the electron injection layer may be a KI:Yb co-deposited layer, an RbI:Yb co-deposited layer, and/or the like.
When the electron injection layer further includes an organic material, alkali metal, alkaline earth metal, rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, alkali metal complex, alkaline earth-metal complex, rare earth metal complex, or any combination thereof may be homogeneously or non-homogeneously dispersed in a matrix including the organic material.
A thickness of the electron injection layer may be in a range of about 1 Å to about 100 Å, and, for example, about 3 Å to about 90 Å. When the thickness of the electron injection layer is within the range described above, suitable or satisfactory electron injection characteristics may be obtained without a substantial increase in driving voltage.
The second electrode 170 may be over the activation layer 140 or the electron transport region as described above. The second electrode 170 may be a cathode, and as the material for the second electrode 170, a metal, an alloy, an electrically conductive compound, or any combination thereof, each having a low work function, may be used.
The second electrode 170 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 170 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.
The second electrode 170 may have a single-layered structure or a multi-layered structure including a plurality of layers.
A first capping layer may be outside the first electrode 110, and/or a second capping layer may be outside the second electrode 170.
The first capping layer and/or second capping layer prevents or reduces entrance of impurities such as water, oxygen, and/or the like into the organic photodetector 10, thereby improving reliability of the organic photodetector 10.
Each of the first capping layer and second capping layer may include a material having a refractive index (at a wavelength of 589 nm) of 1.6 or more.
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 carbocyclic compounds, heterocyclic compounds, amine group-containing compounds, porphyrin derivatives, phthalocyanine derivatives, naphthalocyanine derivatives, alkali metal complexes, alkaline earth metal complexes, or any combination thereof. The carbocyclic compound, the heterocyclic compound, and the amine group-containing compound may be optionally substituted with a substituent containing O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof. In an embodiment, at least one selected from the first capping layer and the second capping layer may each independently include an amine group-containing compound.
In an embodiment, 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 an embodiment, 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, β-NPB, or any combination thereof:
Provided is an electronic apparatus including the organic photodetector as described above. In an embodiment, the electronic apparatus may further include a light-emitting device.
Accordingly, the electronic apparatus according to an embodiment includes: a substrate including a light detection region and an emission region;
an organic photodetector on the light detection region; and
a light-emitting device on the emission region,
wherein the organic photodetector includes: a first pixel electrode; a counter electrode facing the first pixel electrode; and a hole transport region, an activation layer, and an electron transport region, which are sequentially between the first pixel electrode and the counter electrode,
the light-emitting device includes: a second pixel electrode; the counter electrode facing the second pixel electrode; and the hole transport region, an emission layer, and the electron transport region, which are sequentially between the second pixel electrode and the counter electrode,
the first pixel electrode and the activation layer are arranged in correspondence with the light detection region,
the second pixel electrode and the emission layer are arranged in correspondence with the emission region,
the hole transport region, the electron transport region, and the counter electrode are arranged throughout the light detection region and the emission region, and
the activation layer may include a compound represented by Formula 1.
The hole transport region and the electron transport region are respectively the same as described above.
In an embodiment, the hole injection layer, the hole transport layer, the electron transport layer, and/or the electron injection layer; and the counter electrode may be arranged throughout the light detection region and the emission region.
The electronic apparatus may be applied to various suitable displays, light sources, lighting, personal computers (for example, a mobile personal computer), mobile phones, digital cameras, electronic diaries, electronic dictionaries, electronic game machines, medical instruments (for example, electronic thermometers, sphygmomanometers, blood glucose meters, pulse measurement devices, pulse wave measurement devices, electrocardiogram displays, ultrasonic diagnostic devices, and/or endoscope displays), fish finders, various suitable measuring instruments, meters (for example, meters for a vehicle, an aircraft, and/or a vessel), projectors, and/or the like.
Referring to
The substrate 601 and the substrate 602 may be a flexible substrate, a glass substrate, and/or a metal substrate. A buffer layer and a thin-film transistor may be on the substrate 601.
The buffer layer may prevent or reduce penetration of impurities through the substrate 601 and provide a flat surface on the substrate 601. The thin-film transistor may be on the buffer layer and may include an activation layer, a gate electrode, a source electrode, and a drain electrode.
Such a thin-film transistor may be electrically connected to the light-emitting device 500 to drive the light-emitting device 500. One selected from the source electrode and drain electrode may be electrically connected to a second pixel electrode 510 of the light-emitting device 500.
Another thin-film transistor may be electrically connected to the organic photodetector 400. One selected from the source electrode and drain electrode may be electrically connected to a first pixel electrode 410 of the organic photodetector 400.
The organic photodetector 400 may include the first pixel electrode 410, a hole injection layer 420, a hole transport layer 432, an activation layer 440, an electron transport layer 450, and a counter electrode 470.
In an embodiment, the first pixel electrode 410 may be an anode, and the counter electrode 470 may be a cathode. For example, as the organic photodetector 400 is driven by applying a reverse bias across the first pixel electrode 410 and the counter electrode 470, the electronic apparatus 100 may detect light incident onto the organic photodetector 400, generate charges, and extract the charges as a current.
The light-emitting device 500 may include the second pixel electrode 510, the hole injection layer 420, the hole transport layer 432, an emission layer 540, an electron transport layer 450, and the counter electrode 470.
In an embodiment, the second pixel electrode 510 may be an anode, and the counter electrode 470 may be a cathode. For example, in the light-emitting device 500, holes injected from the second pixel electrode 510 and electrons injected from the counter electrode 470 recombine in the emission layer 540 to generate excitons, which generate light by changing from an excited state to a ground state.
The first pixel electrode 410 and the second pixel electrode 510 are respectively the same as described in connection with the first electrode 110 in the present specification.
A pixel-defining film 405 may be on an edge of the first pixel electrode 410 and on an edge of the second pixel electrode 510. The pixel-defining film 405 may define a pixel region and may electrically insulate between the first pixel electrode 410 and the second pixel electrode 510. The pixel-defining film 405 may include, for example, one or more various suitable organic insulating materials (e.g., a silicon-based material), inorganic insulating materials, and/or organic/inorganic composite insulating materials. The pixel-defining film 405 may be a transmissive film that may transmit visible light or a blocking film that may block or reduce transmission of visible light.
The hole injection layer 420 and the hole transport layer 432, which are common layers, are sequentially on the first pixel electrode 410 and the second pixel electrode 510. The hole injection layer 420 and the hole transport layer 432 are respectively the same as described in the present specification.
The activation layer 440 is on the hole transport layer 432 to correspond to the light detection region. The activation layer 440 is the same as described in the present specification.
The emission layer 540 is on the hole transport layer 432 to correspond to the emission region. The emission layer 540 is the same as described in the present specification. In an embodiment, the light-emitting device 500 may further include, between the second pixel electrode 510 and the emission layer 540, an electron blocking layer arranged in correspondence with the emission region.
As common layers for the entirety of the light detection region and the emission region, the electron transport layer 450 and the counter electrode 470 are sequentially on the activation layer 440 and the emission layer 540. The electron transport layer 450 and the counter electrode 470 are respectively the same as described in connection with the electron transport layer and the second electrode 170 in the present specification.
The hole injection layer 420, the hole transport layer 432, and the electron transport layer 450 may each be located throughout the light detection region and the emission region.
As such, in the electronic apparatus 100, by placing a common layer over the organic photodetector 400 and the light-emitting device 500, a manufacturing process may be reduced, and a functional layer material used in the light-emitting device 500 may also be used in the organic photodetector 400. Thus, the organic photodetector 400 may be in a pixel of the electronic apparatus.
In an embodiment, an electron injection layer may be further included in the electron transport layer 450 and the counter electrode 470.
A capping layer may be on the counter electrode 470. A material for forming the capping layer may include the organic material and/or the inorganic material described herein. The capping layer may serve to protect the organic photodetector 400 and the light-emitting device 500 and to assist effective light emission from the light-emitting device 500.
An encapsulation portion 490 may be on the capping layer. The encapsulation portion 490 may be on the organic photodetector 400 and the light-emitting device 500 to thereby protect the organic photodetector 400 and the light-emitting device 500 from water and/or oxygen. The encapsulation portion 490 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, polyoxy methylene, poly aryllate, hexamethyl disiloxane, an acrylic resin (e.g., polymethyl methacrylate, polyacrylic acid, and/or the like), an epoxy resin (e.g., aliphatic glycidyl ether (AGE) and/or the like), or any combination thereof; or a combination of the inorganic film and the organic film.
The electronic apparatus 100 may be, for example, a display apparatus. The electronic apparatus 100 includes both the organic photodetector 400 and the light-emitting device 500, and thus, may be a display apparatus with a light detection function.
In
Components illustrated in
The first light-emitting device 501 may include a second pixel electrode 511, the hole injection layer 420, the hole transport layer 432, a first emission layer 541, the electron transport layer 450, and the counter electrode 470.
The second light-emitting device 502 may include a third pixel electrode 512, the hole injection layer 420, the hole transport layer 432, a second emission layer 542, the electron transport layer 450, and the counter electrode 470.
The third light-emitting device 503 may include a fourth pixel electrode 513, the hole injection layer 420, the hole transport layer 432, a third emission layer 543, the electron transport layer 450, and the counter electrode 470.
The second pixel electrode 511, the third pixel electrode 512, and the fourth pixel electrode 513 may respectively correspond to a first emission region, a second emission region, and a third emission region, and may respectively be the same as described in connection with the first electrode 110 in the present specification.
The first emission layer 541 may be arranged in correspondence with the first emission region and emit first color light, the second emission layer 542 may be arranged in correspondence with the second emission region and emit second color light, and the third emission layer 543 may be arranged in correspondence with the third emission region and emit third color light.
A maximum emission wavelength of the first color light, a maximum emission wavelength of the second color light, and a maximum emission wavelength of the third color light may be identical to or different from each other. In an embodiment, a maximum emission wavelength of the first color light and a maximum emission wavelength of the second color light may each be longer than a maximum emission wavelength of the third color light.
In an embodiment, 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, but embodiments are not limited thereto. Thus, the electronic apparatus 100a may be capable of full color emission. When a mixed light of the first color light, the second color light, and the third color light is white light, the first color light, the second color light, and the third color light may not be respectively limited to red light, green light, and blue light.
The organic photodetector 400, the first light-emitting device 501, the second light-emitting device 502, and the third light-emitting device 503 may each be a sub-pixel, each forming a pixel. In an embodiment, one pixel may include at least one organic photodetector 400.
The electronic apparatus 100a may be a display apparatus. As the electronic apparatus 100a may include the organic photodetector 400, the first light-emitting device 501, the second light-emitting device 502, and the third light-emitting device 503, the electronic apparatus 100a may be a full-color display apparatus having a light detection function.
In the electronic apparatus 100a shown in
In an embodiment, red light, green light, and blue light may respectively be emitted from the first light-emitting device 501, the second light-emitting device 502, and the third light-emitting device 503.
The electronic apparatus 100a according to an embodiment may have a function of detecting an object being in contact (e.g., physical contact) with the electronic apparatus 100a, for example, a fingerprint of a finger. In an embodiment, as shown in
In an embodiment, as shown in
The layers constituting the hole transport region, the activation layer, and the layers constituting the electron transport region may be formed in a set or specific region by using one or more suitable methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, ink-jet printing, laser printing, and/or laser-induced thermal imaging.
When layers constituting the hole transport region, an activation layer, and layers constituting the electron transport region are each independently formed by vacuum-deposition, the vacuum-deposition may be performed at a deposition temperature in a range of about 100° C. to about 500° C., at a vacuum degree in a range of about 10−8 torr to about 10−3 torr, and at a deposition rate in a range of about 0.01 Angstroms per second (Å/sec) to about 100 Å/sec, depending on the material to be included in each layer and the structure of each layer to be formed.
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 three to sixty carbon atoms, and the term “C1-C60 heterocyclic group,” as used herein, refers to a cyclic group that has one to sixty 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. In an embodiment, the C1-C60 heterocyclic group has 3 to 61 ring-forming atoms.
The term “cyclic group,” as used herein, may include 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 three to sixty 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 one to sixty carbon atoms and includes *—N=*′ as a ring-forming moiety.
In an embodiment,
the C3-C60 carbocyclic group may be i) group T1 or ii) a condensed cyclic group in which two or more groups T1 are condensed together with each other (for example, a cyclopentadiene group, an adamantane group, a norbornane group, a benzene group, a pentalene group, a naphthalene group, an azulene group, an indacene group, an acenaphthylene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a perylene group, a pentaphene group, a heptalene group, a naphthacene group, a picene group, a hexacene group, a pentacene group, a rubicene group, a coronene group, an ovalene group, an indene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, an indenophenanthrene group, or an indenoanthracene group),
the C1-C60 heterocyclic group may be i) group T2, ii) a condensed cyclic group in which two or more groups T2 are condensed 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 (for example, a pyrrole group, a thiophene group, a furan group, an indole group, a benzoindole group, a naphthoindole group, an isoindole group, a benzoisoindole group, a naphthoisoindole group, a benzosilole group, a benzothiophene group, a benzofuran group, a carbazole group, a dibenzosilole group, a dibenzothiophene group, a dibenzofuran group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, a benzosilolocarbazole group, a benzoindolocarbazole group, a benzocarbazole group, a benzonaphthofuran group, a benzonaphthothiophene group, a benzonaphthosilole group, a benzofurodibenzofuran group, a benzofurodibenzothiophene group, a benzothienodibenzothiophene group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzoisoxazole group, a benzothiazole group, a benzoisothiazole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a quinoxaline group, a benzoquinoxaline group, a quinazoline group, a benzoquinazoline group, a phenanthroline group, a cinnoline group, a phthalazine group, a naphthyridine group, an imidazopyridine group, an imidazopyrimidine group, an imidazotriazine group, an imidazopyrazine group, an imidazopyridazine group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzothiophene group, an azadibenzofuran group, etc.),
the π electron-rich C3-C60 cyclic group may be i) group T1, ii) a condensed cyclic group in which two or more groups T1 are condensed together with each other, iii) 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 (for example, the C3-C60 carbocyclic group, a 1H-pyrrole group, a silole group, a borole group, a 2H-pyrrole group, a 3H-pyrrole group, a thiophene group, a furan group, an indole group, a benzoindole group, a naphthoindole group, an isoindole group, a benzoisoindole group, a naphthoisoindole group, a benzosilole group, a benzothiophene group, a benzofuran group, a carbazole group, a dibenzosilole group, a dibenzothiophene group, a dibenzofuran group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, a benzosilolocarbazole group, a benzoindolocarbazole group, a benzocarbazole group, a benzonaphthofuran group, a benzonaphthothiophene group, a benzonaphthosilole group, a benzofurodibenzofuran group, a benzofurodibenzothiophene group, a benzothienodibenzothiophene group, etc.),
the π electron-deficient nitrogen-containing C1-C60 cyclic group may be i) group T4, ii) a condensed cyclic group in which two or more group 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 one another (for example, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzoisoxazole group, a benzothiazole group, a benzoisothiazole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a quinoxaline group, a benzoquinoxaline group, a quinazoline group, a benzoquinazoline group, a phenanthroline group, a cinnoline group, a phthalazine group, a naphthyridine group, an imidazopyridine group, an imidazopyrimidine group, an imidazotriazine group, an imidazopyrazine group, an imidazopyridazine group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzothiophene group, an azadibenzofuran group, etc.),
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,
group T2 may be a furan group, a thiophene group, a 1H-pyrrole group, a silole group, a borole group, a 2H-pyrrole group, a 3H-pyrrole group, an imidazole group, a pyrazole group, a triazole group, a tetrazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, an azasilole group, an azaborole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a tetrazine group, a pyrrolidine group, an imidazolidine group, a dihydropyrrole group, a piperidine group, a tetrahydropyridine group, a dihydropyridine group, a hexahydropyrimidine group, a tetrahydropyrimidine group, a dihydropyrimidine group, a piperazine group, a tetrahydropyrazine group, a dihydropyrazine group, a tetrahydropyridazine group, or a dihydropyridazine group,
group T3 may be a furan group, a thiophene group, a 1H-pyrrole group, a silole group, or a borole group, and
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 to any cyclic group or a polyvalent group (for example, 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. In an embodiment, “a 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.”
In an embodiment, Examples of a monovalent C3-C60 carbocyclic group and a 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 a divalent C3-C60 carbocyclic group and a 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 hydrocarbon monovalent group that has one to sixty carbon atoms, and examples thereof 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, and a tert-decyl group. 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 at a main chain (e.g., in the middle) or at a terminal end (e.g., the terminus) of the C2-C60 alkyl group, and examples thereof include an ethenyl group, a propenyl group, and a butenyl group. The term “C2-C60 alkenylene group,” as used herein, refers to a divalent group having 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 at a main chain (e.g., in the middle) or at a terminal end (e.g., the terminus) of the C2-C60 alkyl group, and examples thereof include an ethynyl group and a propynyl group. The term “C2-C60 alkynylene group,” as used herein, refers to a divalent group having 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 include a methoxy group, an ethoxy group, and an isopropyloxy group.
The term “C3-C10 cycloalkyl group,” as used herein, refers to a monovalent saturated hydrocarbon cyclic group of 3 to 10 carbon atoms, and examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornyl group (or bicyclo[2.2.1]heptyl group), a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, and a bicyclo[2.2.2]octyl group. The term “C3-C10 cycloalkylene group,” as used herein, refers to a divalent group having 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 further includes, in addition to a carbon atom, at least one heteroatom as a ring-forming atom and has 1 to 10 carbon atoms, and examples thereof include a 1,2,3,4-oxatriazolidinyl group, a tetrahydrofuranyl group, and a tetrahydrothiophenyl group. The term “C1-C10 heterocycloalkylene group,” as used herein, refers to a divalent group having 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 three to ten 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 include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. The term “C3-C10 cycloalkenylene group,” as used herein, refers to a divalent group having 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, in addition to a carbon atom, at least one heteroatom as a ring-forming atom, 1 to 10 carbon atoms, and at least one carbon-carbon double bond in the cyclic structure thereof. Examples of the C1-C10 heterocycloalkenyl group include a 4,5-dihydro-1,2,3,4-oxatriazolyl group, a 2,3-dihydrofuranyl group, and a 2,3-dihydrothiophenyl group. The term “C1-C10 heterocycloalkenylene group,” as used herein, refers to a divalent group having 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 having six to sixty carbon atoms, and the term “C6-C60 arylene group,” as used herein, refers to a divalent group having a carbocyclic aromatic system having six to sixty carbon atoms. Examples of the C6-C60 aryl group 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, and an ovalenyl group. When the C6-C60 aryl group and the C6-C60 arylene group each include two or more rings, the rings may be condensed together with each other.
The term “C1-C60 heteroaryl group,” as used herein, refers to a monovalent group having a heterocyclic aromatic system that has, in addition to a carbon atom, at least one heteroatom as a ring-forming atom, and 1 to 60 carbon atoms. The term “C1-C60 heteroarylene group,” as used herein, refers to a divalent group having a heterocyclic aromatic system that has, in addition to a carbon atom, at least one heteroatom as a ring-forming atom, and 1 to 60 carbon atoms. Examples of the C1-C60 heteroaryl group 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, and a naphthyridinyl group. When the C1-C60 heteroaryl group and the C1-C60 heteroarylene group each include two or more rings, the rings may be condensed together with each other.
The term “monovalent non-aromatic condensed polycyclic group,” as used herein, refers to a monovalent group having two or more rings condensed together with each other, only carbon atoms (for example, having 8 to 60 carbon atoms) as ring-forming atoms, and non-aromaticity in its molecular structure when considered as a whole (e.g., is not aromatic when considered as a whole). Examples of the monovalent non-aromatic condensed polycyclic group include an indenyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, an indenophenanthrenyl group, and an indeno anthracenyl group. The term “divalent non-aromatic condensed polycyclic group,” as used herein, refers to a divalent group having substantially the same structure as a monovalent non-aromatic condensed polycyclic group.
The term “monovalent non-aromatic condensed heteropolycyclic group,” as used herein, refers to a monovalent group having two or more rings condensed together with each other, at least one heteroatom, in addition to carbon atoms (for example, including 1 to 60 carbon atoms), as a ring-forming atom, and non-aromaticity in its molecular structure when considered as a whole (e.g., is not aromatic when considered as a whole). Examples of the monovalent non-aromatic condensed heteropolycyclic group include a 9,9-dihydroacridinyl group and a 9H-xanthenyl group. The term “divalent non-aromatic condensed heteropolycyclic group,” as used herein, refers to a divalent group having substantially the same structure as a monovalent non-aromatic condensed heteropolycyclic group.
The term “C6-C60 aryloxy group,” as used herein, indicates —OA102 (wherein A102 is the C6-C60 aryl group), and the term “C6-C60 arylthio group,” as used herein, indicates —SA103 (wherein A103 is the C6-C60 aryl group).
The term “C7-C60 arylalkyl group,” as used herein, refers to -A104A105 (where A104 may be a C1-C54 alkylene group, and A105 may be a C6-C59 aryl group), and the term “C2-C60 heteroarylalkyl group,” as used herein, refers to -A106A107 (where A106 may be a C1-C60 alkylene group, and A107 may be a C1-C60 heteroaryl group).
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 used herein may each independently be: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; a C1-C60 alkyl group; a C2-C60 alkenyl group; a C2-C60 alkynyl group; a C1-C60 alkoxy group; or a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C7-C60 arylalkyl group, or a C2-C60 heteroarylalkyl group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof.
The term “hetero atom,” as used herein, refers to any atom other than a carbon atom. Examples of the heteroatom include O, S, N, P, Si, B, Ge, Se, or any combination thereof.
The term “the third-row transition metal,” as used herein, includes hafnium (Hf), tantalum (Ta), tungsten (W), rhenium (Re), osmium (Os), iridium (Ir), platinum (Pt), gold (Au), and 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 “ter-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”. The “terphenyl group” is a substituted phenyl group having, as a substituent, a C6-C60 aryl group substituted with a C6-C60 aryl group.
An ITO glass substrate (anode) was cut to a size of 50 mm×50 mm×0.5 mm, sonicated in isopropyl alcohol and pure water for 10 minutes in each solvent, and cleaned by irradiation of ultraviolet rays and exposure of ozone thereto for 10 minutes. Then, the glass substrate was mounted to a vacuum-deposition apparatus. HAT-CN was vacuum-deposited on the anode to form a hole injection layer having a thickness of 100 Å, and HT3 was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 1,250 Å.
m-MTDATA was vacuum-deposited on the hole transport layer to form an auxiliary layer having a thickness of 200 Å.
SubPC having a thickness of 200 Å and a C60 fullerene having a thickness of 250 Å were sequentially deposited on the auxiliary layer to form an activation layer.
Next, BAlq was vacuum-deposited thereon to form a buffer layer having a thickness of 50 Å, and ET1 was vacuum-deposited on the buffer layer to form an electron transport layer having a thickness of 300 Å.
LiF was vacuum-deposited on the electron transport layer to form an electron injection layer having a thickness of 10 Å, and then MgAg having a thickness of 100 Å was sequentially deposited thereon to form a cathode, thereby completing manufacture of an organic photodetector.
An organic photodetector was manufactured in substantially the same manner as in Comparative Example 1, except that, in forming the activation layer, Compound N,N′-dioctyl-3,4,9,10-perylenedicarboximide was used instead of the fullerene.
An organic photodetector was manufactured in substantially the same manner as in Comparative Example 1, except that, in forming the activation layer, Compound N,N′-ditridecylperylene-3,4,9,10-tetracarboxylic diimide was used instead of the fullerene.
An organic photodetector was manufactured in substantially the same manner as in Comparative Example 1, except that, in forming the activation layer, SubPC and Compound A01 were co-deposited (at a weight ratio of 50:50) to form an activation layer having a thickness of 450 Å.
An organic photodetector was manufactured in substantially the same manner as in Comparative Example 1, except that, in forming the activation layer, Compound A01 was used instead of the fullerene.
An organic photodetector was manufactured in substantially the same manner as in Comparative Example 1, except that, in forming the activation layer, only Compound A10 was used to form an activation layer having a thickness of 450 Å.
An organic photodetector was manufactured in substantially the same manner as in Comparative Example 1, except that, in forming the activation layer, SubPC was vacuum-deposited to a thickness of 100 Å, SubPC and Compound A14 were co-deposited (50:50) to a thickness of 250 Å, and then Compound A14 was sequentially vacuum-deposited to a thickness of 100 Å, to form an activation layer.
An organic photodetector was manufactured in substantially the same manner as in Comparative Example 1, except that, in forming the activation layer, NPB and Compound A18 were co-deposited (50:50) to form an activation layer having a thickness of 450 Å.
An organic photodetector was manufactured in substantially the same manner as in Comparative Example 1, except that, in forming the activation layer, TDATA and Compound A18 were co-deposited (50:50) to form an activation layer having a thickness of 450 Å.
An organic photodetector was manufactured in substantially the same manner as in Comparative Example 1, except that, in forming the activation layer, a C60 fullerene and Compound A01 were co-deposited (at a weight ratio of 50:50) to form an activation layer having a thickness of 450 Å.
An organic photodetector was manufactured in substantially the same manner as in Comparative Example 1, except that a C60 fullerene having a thickness of 200 Å and Compound A01 having a thickness of 250 Å were sequentially deposited on the auxiliary layer to form an activation layer.
External quantum efficiency (EQE) with respect to a wavelength ranging from 580 nm to 590 nm, which is a peak wavelength of each of the organic photodetectors manufactured in Comparative Examples 1 to 3 and Example 2, was measured, and results thereof are shown in Table 1.
Referring to Table 1, it can be seen that Example 2 showed superior EQE to Comparative Examples 1 to 3 in the same device structure.
In an embodiment, EQE with respect to a wavelength of each of the organic photodetectors manufactured in Comparative Example 1 and Examples 1 and 2 was measured, and results thereof are shown in
Referring to
EQE with respect to a wavelength of each of the organic photodetectors manufactured in Examples 1, 2, 3, 5, and 6 was measured, and results thereof are shown in
While the subject matter of the present disclosure has been described with reference to embodiments illustrated in the drawings, these embodiments are provided herein for illustrative purposes only, and one of ordinary skill in the art may understand that the embodiments include various modifications and equivalent embodiments thereof. Accordingly, the true scope of the present disclosure should be determined by the scope of the appended claims, and equivalents thereof.
The organic photodetector according to an embodiment has excellent processability, mass production, and efficiency compared to those of a fullerene by using the compound represented by Formula 1 in the activation layer.
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 of the present disclosure as defined by the following claims, and equivalents thereof.
| Number | Date | Country | Kind |
|---|---|---|---|
| 10-2021-0174013 | Dec 2021 | KR | national |
