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KR-20260065629-A - opto-electronic device, electronic device including the opto-electronic device and electronic apparatus including the electronic device

KR20260065629AKR 20260065629 AKR20260065629 AKR 20260065629AKR-20260065629-A

Abstract

The photoelectric element may include a first electrode; a second electrode facing the first electrode; a photoactive layer disposed between the first electrode and the second electrode; and a fluorine-based compound represented by the chemical formula F: <Chemical Formula F> Among the chemical formula F, Y1 is selected from the group consisting of the group represented by the following chemical formula FY , hydrogen, deuterium, -F, a C1 - C60 alkyl group substituted or unsubstituted with at least one R10a , a C1 - C60 alkoxy group substituted or unsubstituted with at least one R10a , a C3 - C60 carbocyclic group substituted or unsubstituted with at least one R10a, and a C1 - C60 heterocyclic group substituted or unsubstituted with at least one R10a , and Z1 is selected from the group consisting of the group represented by the following chemical formula FZ , hydrogen, deuterium, -F, a C1 - C60 alkyl group substituted or unsubstituted with at least one R10a , a C1 - C60 alkoxy group substituted or unsubstituted with at least one R10a , a C3 - C60 carbocyclic group substituted or unsubstituted with at least one R10a, and a C1 - C60 heterocyclic group substituted or unsubstituted with at least one R10a , and <Chemical Formula FY> Chemical Formula FZ Among chemical formulas F, FY and FZ, Ar 1 to Ar 6 are independently selected from the group consisting of C 6 -C 60 aryl groups substituted with two or more -F and C 2 -C 60 heteroarylalkyl groups substituted with two or more -F, and Refer to the present specification for the description of L 1 , L 2 , L 31 to L 35 and L 4 , n1, n2, n31 to n35 and n4, T 1 , a1, and R 10a .

Inventors

  • 김기웅
  • 윤석규
  • 자히드 하산 시에드
  • 백세연
  • 정대성
  • 강민균

Assignees

  • 삼성디스플레이 주식회사
  • 포항공과대학교 산학협력단

Dates

Publication Date
20260511
Application Date
20241029

Claims (20)

  1. First electrode; A second electrode facing the first electrode; A photoactive layer disposed between the first electrode and the second electrode; and A photoelectric device comprising a fluorine-based compound represented by the following chemical formula F: <Chemical Formula F> Among the above chemical formula F, Y1 is selected from the group consisting of the group represented by the following chemical formula FY , hydrogen, deuterium, -F, a C1 - C60 alkyl group substituted or unsubstituted with at least one R10a , a C1 - C60 alkoxy group substituted or unsubstituted with at least one R10a , a C3 - C60 carbocyclic group substituted or unsubstituted with at least one R10a, and a C1 - C60 heterocyclic group substituted or unsubstituted with at least one R10a , and Z1 is selected from the group consisting of the group represented by the following chemical formula FZ , hydrogen, deuterium, -F, a C1 - C60 alkyl group substituted or unsubstituted with at least one R10a , a C1 - C60 alkoxy group substituted or unsubstituted with at least one R10a , a C3 - C60 carbocyclic group substituted or unsubstituted with at least one R10a, and a C1 - C60 heterocyclic group substituted or unsubstituted with at least one R10a , and <Chemical Formula FY> Chemical Formula FZ Among the above chemical formulas F, FY, and FZ, Ar 1 to Ar 6 are independently selected from the group consisting of C 6 -C 60 aryl groups substituted with two or more -F and C 2 -C 60 heteroarylalkyl groups substituted with two or more -F, and L1 , L2 , L31 to L35 and L4 are independently C1 - C20 alkylene groups substituted or unsubstituted with at least one R10a , and n1, n2, n31 to n35 and n4 are independently 0 or 1, and T 1 is O or S, and a1 is selected from integers from 0 to 10, and R 10a is, Deuterium (-D), -F, -Cl, -Br, -I, hydroxyl group, cyano group, or nitro group; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C3 - C60 carbocyclic group, C1 - C60 heterocyclic group, C6 - C60 aryloxy group, C6 - C60 arylthio group, C7 - C60 arylalkyl group, 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, C1 - C60 alkyl group, C2 -C60 alkenyl group, C2 - C60 alkynyl group, or C1 - C60 alkoxy group; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C1 - C60 alkyl group, C2 - C60 alkenyl group, C2 - C60 alkynyl group, C1 - C60 alkoxy group, C3 - C60 carbocyclic group, C1 - C60 heterocyclic group, C6 - C60 aryloxy group, C6 - C60 arylthio group, C7 - C60 arylalkyl group, C2 - C60 heteroarylalkyl group, -Si( Q21 )( Q22 )( Q23 ), -N( Q21 )( Q22 ), -B( Q21)(Q22 ) , -C(=O)( Q21 ), -S(=O) 2 (Q 21 ), -P(=O)(Q 21 )(Q 22 ), or any combination thereof, substituted or unsubstituted with a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 7 -C 60 arylalkyl group, or a C 2 -C 60 heteroarylalkyl group; or -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O) 2 (Q 31 ), or -P(=O)(Q 31 )(Q 32 ), Q1 to Q3 , Q11 to Q13 , Q21 to Q23 , and Q31 to Q33 are independently of each other. Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C1 - C60 alkyl group, C2 - C60 alkenyl group, C2 - C60 alkynyl group, C1 - C60 alkoxy group, or A C3 - C60 carbocyclic group, C1 - C60 heterocyclic group, C7 - C60 arylalkyl group, or C2-C60 heteroarylalkyl group substituted or unsubstituted with deuterium, -F, cyano group, C1 - C60 alkyl group, C1 - C60 alkoxy group, phenyl group , biphenyl group, or any combination thereof, and * is a bonding site with a neighboring atom.
  2. In paragraph 1, The above photoactive layer is a photoelectric device comprising the above fluorine-based compound.
  3. In paragraph 1, A photoelectric device further comprising a first compound that is different from the above-mentioned fluorine-based compound and absorbs light having a wavelength of 400 nm to 1000 nm.
  4. In paragraph 3, The above photoactive layer comprises a fluorine layer; and a first layer disposed between the first electrode and the fluorine layer, and The above fluorine layer comprises the above fluorine-based compound, and The first layer above is a photoelectric device comprising the first compound.
  5. In paragraph 4, A photoelectric device in which the thickness of the above fluorine layer is smaller than the thickness of the above first layer.
  6. In paragraph 1, A photoelectric device comprising a second compound that is different from the above-mentioned fluorine-based compound and is not a fullerene-based compound.
  7. In paragraph 6, The above photoactive layer comprises a second layer; and a fluorine layer disposed between the first electrode and the second layer, and The above fluorine layer comprises the above fluorine-based compound, and The above second layer is a photoelectric device comprising the above second compound.
  8. In Paragraph 7, A photoelectric device in which the thickness of the above fluorine layer is smaller than the thickness of the above second layer.
  9. In paragraph 1, The above fluorine-based compound is a photovoltaic device that does not contain -Cl, -Br, -I, and cyano groups.
  10. In paragraph 1, Among the above chemical formulas F, FY, and FZ, A photovoltaic device in which Ar 1 to Ar 6 are independently selected from the group consisting of C 6 -C 60 aryl groups substituted with 5 or more -F and C 2 -C 60 heteroarylalkyl groups substituted with 5 or more -F.
  11. In paragraph 1, Among the above chemical formulas F, FY, and FZ, A photoelectric element in which Ar 1 to Ar 6 are independently substituted with 2 or more -F groups, phenyl group; naphthyl group; anthracenyl group; phenanthrenyl group; tetracenyl group; chrysenyl group; pyrenyl group; pyridinyl group; pyrimidinyl group; triazinyl group; pyrazinyl group; quinolinyl group; isoquinolinyl group; quinazolinyl group; or quinoxalinyl group.
  12. In paragraph 1, A photoelectric device in which, among the above formulas F, FY, and FZ, n1, n2, n31 to n35, and n4 are each 1.
  13. In paragraph 1, A photoelectric device in which T1 is O in the above chemical formula FY.
  14. In paragraph 1, A photoelectric element in which, in the above chemical formula FY, a1 is an integer selected from 0 to 3.
  15. In paragraph 1, The above-mentioned fluorine compound is any one of the following compounds F1 to F4, a photoelectric device: .
  16. An electronic device including a photoelectric element according to paragraph 1.
  17. In Paragraph 16, An electronic device further comprising a light-emitting element including a light-emitting layer disposed between the first electrode and the second electrode, which is non-overlapping with the photoactive layer.
  18. In Paragraph 17, The above photoelectric device further comprises a first hole transport region disposed between the first electrode and the photoactive layer; and a first electron transport region disposed between the photoactive layer and the second electrode. The above-described light-emitting element further comprises a second hole transport region disposed between the first electrode and the light-emitting layer; and a second electron transport region disposed between the light-emitting layer and the second electrode.
  19. In Paragraph 18, The above first hole transport region and the above second hole transport region are a common layer, and An electronic device in which the first electron transport region and the second electron transport region are a common layer.
  20. Includes electronic devices pursuant to Paragraph 16, An electronic device that is one of a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, a light for indoor or outdoor lighting and/or signaling, a head-up display, a fully or partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a telephone, a mobile phone, a tablet, a phablet, a personal information terminal (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a microdisplay, a 3D display, a virtual reality or augmented reality display, a vehicle, a video wall including multiple displays tiled together, a theater or stadium screen, a light therapy device, and a signboard.

Description

opto-electronic device, electronic device including the opto-electronic device and electronic apparatus including the electronic device This relates to photoelectric elements, electronic devices including the same, and electronic equipment. A photovoltaic device is a device that converts light energy or light signals into electrical energy or electrical signals. Examples of photovoltaic devices include photocells or solar cells that convert light energy into electrical energy, and photodetectors or photosensors that detect light energy and convert it into electrical signals. Electronic devices including photovoltaic and light-emitting elements are being developed. Light emitted from a light-emitting element may be reflected from an object in contact with the electronic device (e.g., a user's finger) and incident on the photovoltaic element. As the photovoltaic element detects the incident light energy and converts it into an electrical signal, it can be recognized that an object has come into contact with or approached the electronic device. Compared to the magnitude of the voltage applied to the light-emitting element, the magnitude of the voltage applied to the photovoltaic element (e.g., reverse voltage) can be applied small, and for reasons such as process costs, some components applied to the light-emitting element (e.g., hole transport region and/or electron transport region) are applied to the photovoltaic element as a common layer. There is a demand for a photovoltaic element in which the amount of charge reaching the electrode through a thick common layer is improved even under low voltage. FIG. 1 is a schematic diagram showing a photoelectric element according to one embodiment of the present invention. FIG. 2 is a schematic diagram showing a photoelectric element according to another embodiment of the present invention. FIG. 3 is a schematic diagram showing a photoelectric element according to another embodiment of the present invention. FIG. 4 is a schematic diagram showing a light-emitting element included in an electronic device according to one embodiment. FIG. 5 is a cross-sectional view of an electronic device according to one embodiment of the present invention. FIG. 6 is a cross-sectional view of an electronic device according to another embodiment of the present invention. FIG. 7 is a perspective view schematically illustrating an electronic device including a photoelectric element according to one embodiment of the present invention. FIG. 8 is a schematic diagram illustrating the exterior of a vehicle as an electronic device including a photoelectric element according to one embodiment of the present invention. FIGS. 9a to 9c are schematic drawings illustrating the interior of a vehicle according to various embodiments of the present invention. FIGS. 10a to 10c are drawings showing the results according to Evaluation Example 1. In the present specification, the phrase “the photoelectric element, the photoactive layer and/or the fluorine layer comprises a fluorine-based compound represented by the formula F” may be interpreted as “the photoelectric element, the photoactive layer and/or the fluorine layer comprises one fluorine-based compound belonging to the category of the formula F” or “the photoelectric element, the photoactive layer and/or the fluorine layer comprises two or more different fluorine-based compounds belonging to the category of the formula F”. According to one aspect, a photoelectric device is provided comprising: a first electrode; a second electrode facing the first electrode; a photoactive layer disposed between the first electrode and the second electrode; and a fluorine-based compound represented by the following formula F: <Chemical Formula F> Among the above chemical formula F, Y1 is selected from the group consisting of the group represented by the following chemical formula FY , hydrogen, deuterium, -F, a C1 - C60 alkyl group substituted or unsubstituted with at least one R10a , a C1 - C60 alkoxy group substituted or unsubstituted with at least one R10a , a C3 - C60 carbocyclic group substituted or unsubstituted with at least one R10a, and a C1 - C60 heterocyclic group substituted or unsubstituted with at least one R10a , and Z1 is selected from the group consisting of the group represented by the following chemical formula FZ , hydrogen, deuterium, -F, a C1 - C60 alkyl group substituted or unsubstituted with at least one R10a , a C1 - C60 alkoxy group substituted or unsubstituted with at least one R10a , a C3 - C60 carbocyclic group substituted or unsubstituted with at least one R10a, and a C1 - C60 heterocyclic group substituted or unsubstituted with at least one R10a , and <Chemical Formula F-Y> Chemical Formula F-Z Among the above chemical formulas F, F-Y and F-Z, Ar 1 to Ar 6 are independently selected from the group consisting of C 6 -C 60 aryl groups substituted with two or more -F and C 2 -C 60 heteroarylalkyl groups substituted with two or more -F, an