Organic photoelectronic device and image sensor

{
  "publication_number": "US10256414B2",
  "country": "US",
  "kind": "B2",
  "title": "Organic photoelectronic device and image sensor",
  "abstract": "Disclosed are an organic photoelectronic device including a first electrode and a second electrode facing each other and an active layer interposed between the first electrode and the second electrode, wherein the active layer includes a p-type semiconductor compound represented by the formula C 22 R 1 - R 12 O 2 N 2 and an n-type semiconductor compound having a maximum absorption peak at a wavelength region of about 500 nm to about 600 nm, and an image sensor including the organic photoelectronic device.",
  "claims": [
    "1. An organic photoelectronic device, comprising a first electrode and a second electrode, and an active layer between the first electrode and the second electrode, wherein the active layer comprises a p-type semiconductor compound represented by Chemical Formula 1, and an n-type semiconductor compound having a maximum absorption peak in a wavelength region of about 500 nm to about 600 nm and represented by Chemical Formula 2: wherein R 1 and R 2 are independently hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group having electron donating characteristics, or a combination thereof, R 3 and R 4 are independently a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group having electron donating characteristics, or a combination thereof, and R 5 to R 12 are independently hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a substituted or unsubstituted C1 to C30 alkoxy group, a halogen atom, a halogen-containing group, or a combination thereof, wherein R a to R 1 are independently hydrogen, a substituted or unsubstituted C1 to C30alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a halogen atom, a halogen-containing group, or a combination thereof, and X is an anion; wherein the active layer comprises an intrinsic layer including the p-type semiconductor compound and the n-type semiconductor compound in a thickness ratio of about 1:10 to about 10:1.",
    "2. The organic photoelectronic device of claim 1, wherein R 3 and R 4 are independently a linear C1 to C10 alkyl group.",
    "3. The organic photoelectronic device of claim 2, wherein R 1 and R 2 are independently a linear C1 to C10 alkyl group.",
    "4. The organic photoelectronic device of claim 1, wherein the compound represented by Chemical Formula 1 is a compound represented by Chemical Formula 1a: wherein, in Chemical Formula 1a, R 1 to R 4 are independently a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group having electron donating characteristics, or a combination thereof.",
    "5. The organic photoelectronic device of claim 4, wherein R 1 to R 4 of Chemical Formula 1a are independently a linear C1 to C10 alkyl group.",
    "6. The organic photoelectronic device of claim 4, wherein the compound represented by Chemical Formula 1a is represented by Chemical Formula 1aa or 1ab:",
    "7. The organic photoelectronic device of claim 1, wherein the p-type semiconductor compound has a thermal decomposition temperature that is greater than or equal to about 300 ° C.",
    "8. The organic photoelectronic device of claim 1, wherein the p-type semiconductor compound has an extinction coefficient that is greater than or equal to about 30,000 cm −1 at a maximum absorption wavelength (λ max).",
    "9. The organic photoelectronic device of claim 1, wherein at least one of R a to R l comprises a halogen atom, and at least one of R m to R u comprises a halogen atom.",
    "10. The organic photoelectronic device of claim 1, wherein the compound represented by Chemical Formula 2 comprises at least one of the compounds represented by Chemical Formulae 2a to 2e:",
    "11. The organic photoelectronic device of claim 1, wherein the active layer comprises at least one of a p-type layer including the p-type semiconductor compound and an n-type layer including the n-type semiconductor compound.",
    "12. The organic photoelectronic device of claim 1, wherein the active layer comprises a p-type layer including the p-type semiconductor compound and an n-type layer including the n-type semiconductor compound.",
    "13. The organic photoelectronic device of claim 1, further comprising a charge auxiliary layer positioned at least one of between the first electrode and the active layer and between the second electrode and the active layer.",
    "14. The organic photoelectronic device of claim 1, wherein the first electrode and the second electrode are transparent electrodes.",
    "15. An image sensor including the organic photoelectronic device of claim 1.",
    "16. The image sensor of claim 15, wherein the organic photoelectronic device is configured to selectively absorb light of a green wavelength region.",
    "17. The image sensor of claim 16, wherein the image sensor comprises a red pixel, a green pixel, and a blue pixel, the red pixel comprises a red filter and a red photo-sensing device, the green pixel comprises a green photo-sensing device electrically connected to the organic photoelectronic device, and the blue pixel comprises a blue filter and a blue photo-sensing device."
  ],
  "description_excerpt": "This application claims priority from Korean Patent Application No. 10-2013-0151095, filed in the Korean Intellectual Property Office on Dec. 6, 2013, the entire contents of which are incorporated herein by reference.\n\n1. Field\n\nExample embodiments of an organic photoelectronic device and of an image sensor including the same are disclosed.\n\n2. Description of the Related Art\n\nA photoelectronic device converts light into an electrical signal using photoelectronic effects, and may include a photodiode, a phototransistor, and the like, and may be applied to an image sensor, a solar cell, and the like.\n\nAn image sensor including a photodiode typically requires high resolution and thus a small pixel size. Currently, a silicon photodiode is widely used, but presents the disadvantage of deteriorated sensitivity because of a small absorption area due to small pixels. Accordingly, an organic material that is capable of replacing silicon has been researched.\n\nThe organic material has a high extinction coefficient and selectively absorbs light in a particular wavelength region depending on a molecular structure, and thus may simultaneously replace a photodiode and a color filter and, as a result, improve sensitivity and contribute to high integration.\n\nOne example embodiment provides an organic photoelectronic device that selectively absorbs light in a green wavelength region and improves efficiency and thermal stability.\n\nAnother example embodiment provides an image sensor including the organic photoelectronic device.",
  "cpc": [
    "H10K 39/32",
    "C07D 471/04",
    "H01L 2251/308",
    "H01L 27/307",
    "H01L 51/001",
    "H01L 51/0072",
    "H01L 51/008",
    "H01L 51/4253",
    "H10F 39/12",
    "H10K 2102/103",
    "H10K 30/30",
    "H10K 71/164",
    "H10K 85/322",
    "H10K 85/6572",
    "Y02E 10/549"
  ],
  "ipc": [
    "H10K 99/00"
  ],
  "assignees": [
    "Samsung Electronics Co Ltd"
  ],
  "inventors": [
    "Seon-Jeong Lim",
    "Kyung Bae Park",
    "Dong-seok Leem",
    "Moon Gyu Han",
    "Kyu Sik KIM",
    "Takkyun RO",
    "Kwang Hee Lee",
    "Yong Wan JIN",
    "Chul Joon HEO"
  ],
  "filing_date": "2014-10-23",
  "publication_date": "2019-04-09",
  "grant_date": "2019-04-09",
  "priority_date": "2013-12-06",
  "application_number": "US-201414521840-A",
  "family_id": "53272068",
  "cited_by_count": 11,
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}