IP Library › Granted Patent US 10,529,937
Granted Patent B2
US 10,529,937 · App. 15/578,483 · Granted Jan 7, 2020

Method of manufacturing organic semiconductor device

Inventors: Do Hwan Kim (Anyang-si, KR); Moon Sung Kang (Seoul, KR); Haejung Hwang (Seoul, KR); Han Wool Park (Seoul, KR); Ji Hye Shin (Seoul, KR)
Assignees: FOUNDATION OF SOONGSIL UNIVERSITY-INDUSTRY COOPERATION; IUCF-HYU (INDUSTRY-UNIVERSITY COOPERATION FOUNDATION HANYANG UNIVERSITY)
H01L51/0566C09D5/24C09D7/63C09D165/00H01L51/0007H01L51/0028H01L51/0035H01L51/0541H01L51/0545C08G2261/3223C08G2261/3243C08G2261/334C08G2261/51C08G2261/92C08K5/5406C08K5/5455H01L51/0562
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Quick Facts
Patent No.
US 10,529,937
App. No.
15/578,483
Granted
Jan 7, 2020
Kind
B2
Abstract

According to embodiments of the present invention, a method of manufacturing an organic semiconductor device includes forming a first organic semiconductor layer on a substrate, and forming a self-assembled monolayer by providing a self-assembly precursor onto the first organic semiconductor layer. The first organic semiconductor layer has a reactive group on a top surface of the first organic semiconductor layer. The forming of the self-assembled monolayer includes forming a chemical bond between the self-assembly precursor and the reactive group of the first organic semiconductor layer.

Claims (37)

1. A method of manufacturing an organic semiconductor device, the method comprising:

forming a first organic semiconductor layer on a substrate, the first organic semiconductor layer having a reactive group on a top surface of the first organic semiconductor layer; and

forming a self-assembled monolayer by providing a self-assembly precursor onto the first organic semiconductor layer,

wherein the forming of the first organic semiconductor layer comprises applying an organic semiconductor solution to a top surface of the substrate,

wherein the organic semiconductor solution comprises an organic semiconductor material and an organometallic precursor,

wherein the organometallic precursor includes a plurality of organometallic precursors,

wherein the forming of the first organic semiconductor layer further comprises reacting the organometallic precursors with each other to form a network structure, and

wherein the forming of the self-assembled monolayer comprises forming a chemical bond between the self-assembly precursor and the reactive group of the first organic semiconductor layer.

2. The method of claim 1 , wherein the self-assembled monolayer has a functional group on a top surface of the self-assembled monolayer, and

wherein the functional group of the self-assembled monolayer is different from the reactive group of the first organic semiconductor layer.

3. The method of claim 1 ,

wherein the organometallic precursor is represented by the following chemical formula 1,

wherein

“M 1 ” and “M 2 ” each independently include at least one of Sc, Ti, V, Cr, Mn, Fe, Co, Ni, Si, Cu, Zn, Pd, Ag, Au, Hg, Pt, Ta, Mo, Zr, Ta, Mg, Sn, Ge, Y, Nb, Tc, Ru, Rh, Lu, Hf, W, Re, Os, Ir, Lr, Rf, Db, Sg, Bh, Hs, Mt, Ds, Rg, or Uub,

“Y” is one of a substituted or unsubstituted C1 to C30 alkyl group, a C3 to C30 cyclo alkyl group, a C3 to C30 heterocyclic group, a C2 to C30 alkenyl group, a C3 to C30 cycloalkenyl group, a C2 to C30 alkynyl group, a C1 to C30 alkoxy group, a C1 to C30 alkylthio group, a C3 to C30 arylether group, a C3 to C30 arylthioether group, a C3 to C30 aryl group, a C3 to C30 heteroaryl group, a halogen atom, a cyano group, a formyl group, a C1 to C30 alkylcarbonyl group, a C3 to C30 arylcarbonyl group, a carboxyl group, a C1 to C30 alkoxycarbonyl group, a C3 to C30 aryloxycarbonyl group, a C1 to C30 alkylcarbonyloxy group, a C1 to C30 arylcarbonyloxy group, a carbamoyl group, an amino group, and a silyl group,

“X 1 ” and “X 2 ” are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a C3 to C30 cycloalkyl group, a C3 to C30 heterocyclic group, a C2 to C30 alkenyl group, a C3 to C30 cycloalkenyl group, a C2 to C30 alkynyl group, a C1 to C30 alkoxy group, a C1 to C30 alkylthio group, a C3 to C30 arylether group, a C3 to C30 arylthioether group, a C3 to C30 aryl group, a C3 to C30 heteroaryl group, a halogen atom, a cyano group, a formyl group, a C1 to C30 alkylcarbonyl group, a C3 to C30 arylcarbonyl group, a carboxyl group, a C1 to C30 alkoxycarbonyl group, a C3 to C30 aryloxycarbonyl group, a C1 to C30 alkylcarbonyloxy group, a C1 to C30 arylcarbonyloxy group, a carbamoyl group, an amino group, and a hydroxy group, and

the substituted alkyl group includes an alkyl group substituted with a halogen element.

4. The method of claim 3 , further comprising:

forming an insulating layer between the substrate and the first organic semiconductor layer,

wherein the insulating layer has a functional group on a top surface of the insulating layer, and

wherein the forming of the first organic semiconductor layer further comprises: bonding the organometallic precursor to the functional group of the insulating layer.

5. The method of claim 4 , further comprising:

forming a gate pattern between the substrate and the insulating layer; and

forming a source/drain pattern on the first organic semiconductor layer.

6. The method of claim 1 , further comprising:

forming an insulating layer on the self-assembled monolayer;

forming a gate pattern on the insulating layer; and

forming a source/drain pattern between the substrate and the first organic semiconductor layer.

7. The method of claim 1 , wherein the self-assembly precursor is represented by the following chemical formula 2,

wherein

“A” includes one of —NH 2 , —SH, —COOH, —CF 3 , and a halogen element, wherein the halogen element includes one of F, Cl, Br, and I,

“R” is one of a substituted or unsubstituted C1 to C30 alkyl group, a C3 to C30 cycloalkyl group, a C3 to C30 heterocyclic group, a C2 to C30 alkenyl group, a C3 to C30 cycloalkenyl group, a C2 to C30 alkynyl group, a C1 to C30 alkoxy group, a C1 to C30 alkylthio group, a C3 to C30 arylether group, a C3 to C30 arylthioether group, a C3 to C30 substituted or unsubstituted aryl group, a C3 to C30 heteroaryl group, a halogen atom, a cyano group, a formyl group, a C1 to C30 alkylcarbonyl group, a C3 to C30 arylcarbonyl group, a carboxyl group, a C1 to C30 alkoxycarbonyl group, a C3 to C30 aryloxycarbonyl group, a C1 to C30 alkylcarbonyloxy group, a C1 to C30 arylcarbonyloxy group, a carbamoyl group, a substituted or unsubstituted thiophene, an amino group, and a hydroxy group,

“n” is an integral number between 0 and 30,

“M 3 ” includes at least one of Sc, Ti, V, Cr, Mn, Fe, Co, Ni, Si, Cu, Zn, Pd, Ag, Au, Hg, Pt, Ta, Mo, Zr, Ta, Mg, Sn, Ge, Y, Nb, Tc, Ru, Rh, Lu, Hf, W, Re, Os, Jr, Lr, Rf, Db, Sg, Bh, Hs, Mt, Ds, Rg, or Uub,

groups represented by “X 3 ” are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a C3 to C30 cycloalkyl group, a C3 to C30 heterocyclic group, a C2 to C30 alkenyl group, a C3 to C30 cycloalkenyl group, a C2 to C30 alkynyl group, a C1 to C30 alkoxy group, a C1 to C30 alkylthio group, a C3 to C30 arylether group, a C3 to C30 arylthioether group, a C3 to C30 aryl group, a C3 to C30 heteroaryl group, a halogen atom, a cyano group, a formyl group, a C1 to C30 alkylcarbonyl group, a C3 to C30 arylcarbonyl group, a carboxyl group, a C1 to C30 alkoxycarbonyl group, a C3 to C30 aryloxycarbonyl group, a C1 to C30 alkylcarbonyloxy group, a C1 to C30 arylcarbonyloxy group, a carbamoyl group, an amino group, and a hydroxy group, and

the substituted alkyl group of “X 3 ” includes an alkyl group substituted with a halogen element.

8. The method of claim 1 , wherein the chemical bond includes a silanol bond.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 19, 2018
From: FOUNDATION OF SOONGSIL UNIVERSITY-INDUSTRY COOPERATION
To: FOUNDATION OF SOONGSIL UNIVERSITY-INDUSTRY COOPERATION; INDUSTRY-UNIVERSITY COOPERATION FOUNDATION HANYANG UNIVERSITY
Reel/Frame 047536/0911 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 1, 2017
From: KIM, DO HWAN; KANG, MOON SUNG; HWANG, HAEJUNG; PARK, HAN WOOL; SHIN, JI HYE
To: FOUNDATION OF SOONGSIL UNIVERSITY-INDUSTRY COOPERATION
Reel/Frame 044275/0897 →
Priority Claims (5)
KR 10-2016-0079962 · Jun 27, 2016 · national
KR 10-2016-0082390 · Jun 30, 2016 · national
KR PCT/KR2016/014290 · Dec 7, 2016 · national
KR PCT/KR2017/000461 · Jan 13, 2017 · national
KR 10-2017-0079382 · Jun 22, 2017 · national
Continuity (1)
Related Publication 20180315938A1 · Nov 1, 2018