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TCI Confidential © 2020 1

Technical Webinar

Organic Transistor

Device Fabrication / EvaluationAnd

High-Quality Organic Semiconductors (HQOS)

Nov. 26, 2020

Tokyo Chemical Industry (TCI)Organic Electronics

Material Development GroupDevice Evaluation Team

Yuji Yamaguchi

TCI Confidential © 2020 2

Speaker information

Dr. Yuji Yamaguchi

Team Leader,

Device Evaluation Team,

Organic Electronics Material Development,

Oji R&D

Career

• 2013 Ph.D. degree in engineering at Yamagata university.

• 2013 - 2016 Postdoctoral researcher, JST-CREST, Yamagata University.

• 2016 - present Tokyo Chemical Industry Co., LTD. (TCI).

Research Topics

• Materials Science

• Nanotechnology

• Organic Electronics

• Organic Transistors

• Organic Solar Cells

Organic Transistors Organic Solar Cells

-Previous works-

Terazulene Isomers: Polarity Change of OFETs Through Molecular Orbital

Distribution Contrast

Yuji Yamaguchi, Maki Takubo, Keisuke Ogawa, Ken-ichi Nakayama, Tomoyuki

Koganezawa, and Hiroshi Katagiri*

Journal of the American Chemical Society, 2016, 138, 11335-11343.

Terazulene: A High-Performance n-Type Organic Field-Effect Transistor Based

on Molecular Orbital Distribution Control

Yuji Yamaguchi, Keisuke Ogawa, Ken-ichi Nakayama*, Yoshihiro Ohba, and Hiroshi

Katagiri*

Journal of the American Chemical Society, 2013, 135, 19095-19098.

Photoprecursor approach as an effective

means for preparing multilayer organic

semiconducting thin films by solution processes

Yuji Yamaguchi, Mitsuharu Suzuki, Takao

Motoyama, Shuhei Sugii, Chiho Katagiri, Katsuya

Takahira, Shinya Ikeda, Hiroko Yamada, Ken-ichi

Nakayama;Sci. Rep. 2014, 4, DOI: 10.1038/srep07151

TCI Confidential © 2020 3

Topics

1. Introduction

• Tokyo Chemical Industry (TCI)

• Organic Electronics

2. New attempt for high quality semiconductor products

3. Fabrication and evaluation of OFET devices

“Fundamental materials”

• 「Pentacene」• 「P3HT」

“High-performance materials”

• 「Ph-BTBT-n series」• 「TU-n series」

TCI Confidential © 2020 4

Topics

1. Introduction

• Tokyo Chemical Industry (TCI)

• Organic Electronics

2. New attempt for high quality semiconductor products

3. Fabrication and evaluation of OFET devices

“Fundamental materials”

• 「Pentacene」• 「P3HT」

“High-performance materials”

• 「Ph-BTBT-n series」• 「TU-n series」

TCI Confidential © 2020 5

Tokyo Chemical Industry

Fukaya Factory

(Fukaya City,Saitama)

TCI Confidential © 2020 6

Synthetic Reagents

Building Blocks

Catalysis, etc.

Electronic Materials

Photonic and Optical Materials

Nanocarbon Materials, etc.

Biochemicals

Glycoscience

Antibodies, etc.

Analytical Reagents

Liquid Chromatography

Gas Chromatography, etc.

Categories Product lineup: 30,000

TCI Confidential © 2020 7

Pentacene 99.999%[P2524]

Ph-BTBT-10 >99.5%

[D5491]

[5], [6], [7], [8], [9], [10], [12] CPPs[C2931][C3386][C3571][C3544][C3465][C3493[C2449]

Carbon Nanobelt[I1078]

P3HTRegioregular >99%

[P2513]

Dibenzopentacene[D5488]

[M2088] [P2013] [P2014] [P2015]C60, C70

[B1641] [B1694]HN-D2[B4907]

HN-D1[B4908]

V886[V0146]

Corannulene[C2572]

Sumanene[S0888]

Organic Electronics Materials

TCI Confidential © 2020 8

Topics

1. Introduction

• Tokyo Chemical Industry (TCI)

• Organic Electronics

2. New attempt for high quality semiconductor products

3. Fabrication and evaluation of OFET devices

“Fundamental materials”

• 「Pentacene」• 「P3HT」

“High-performance materials”

• 「Ph-BTBT-n series」• 「TU-n series」

TCI Confidential © 2020 9

Organic Electronics

LG

lighting

SUMITOMO CHEMICAL

Mitsubishi Chemical

Organic Transistors

Organic Light Emitting Devices(OLED) Organic Solar Cells

Organic Semiconductor Materials

TCI Confidential © 2020 10

10

Organic Transistors

Ultra-thin filmand lightweight

Yamagata UniversityTokito Lab.

Device configuration

Side view Top view

Electrode(Drain)

Electrode (Source)

Electrode (Gate)

Insulator

TCI Confidential © 2020 11

Toward practical use of “Organic Transistors”

TCI offers

“High Quality Organic Semiconductor Materials”

specialized for electrical performance.

①Development of

Semiconductor Materials

②Development of

Fabrication Processes

③Development of

Applications

TCI Confidential © 2020 12

Topics

1. Introduction

• Tokyo Chemical Industry (TCI)

• Organic Electronics

2. New attempt for high quality semiconductor products

3. Fabrication and evaluation of OFET devices

“Fundamental materials”

• 「Pentacene」• 「P3HT」

“High-performance materials”

• 「Ph-BTBT-n series」• 「TU-n series」

TCI Confidential © 2020 13

To contribute to the material science through

high-pure synthesis, quality assurance and stable supply

Our Mission

Organic Transistor

“Semiconductor materials”

We assess the functionality of the semiconductor materials as a quality

assurance measure to confirm the electronic properties and their device

performance.

TCI Confidential © 2020 14

Simple device structure

▼

One semiconductor

material

Why Organic Transistors?

Organic Transistor

(OFET)

Organic Light Emitting Device

(OLED)Organic Photovoltaic cell

(OPV)

TCI Confidential © 2020 15

What Can It Detect?

Current value

（Slope）▼

Mobility

（performance parameter）

0.0E+00

1.0E-02

2.0E-02

3.0E-02

4.0E-02

5.0E-02

6.0E-02

-50-250

Cur

rent

Voltage

When using a high-quality semiconductor

material, a better mobility can be

detected despite the same molecular

structure.

TCI Confidential © 2020 16

0.0E+00

1.0E-02

2.0E-02

3.0E-02

4.0E-02

5.0E-02

6.0E-02

-50-250

An effect of low amount of impurities on the transistor performance

Obvious difference

in the current values

▼

Both SamplesHPLC: >99.5%

Cur

rent

Voltage

Both purities are over 99.5%

Clear difference in OFET performance

We can offer real “usable material”

Mobility: > 10.0 cm2/Vs(ODTS Si/SiO2 substrate)

What Can It Do?

Mobility:

12.0 cm2/Vs

Mobility:

5.2 cm2/Vs

TCI Confidential © 2020 17

High-Quality Organic Semiconductors (HQOS)

• In this new category, each product is set a mobility* as our original quality standard.

• Every lot of the products are analyzed by the in-house transistor device test.

• Only lots that pass this functional test are packed and shipped as “HQOS”

• We can offer real “usable material” to organic electronics research fields.

Unique points

* The mobility refers to device evaluation measurements obtained within our facility.

TCI Confidential © 2020 18

Product lineup of HQOS

P3HT

[P2513]

Phthalocyanine

[P2734]

CuPc

[C3645]

Pentacene

[P2524]

TIPS-Pentacene

[B5942]

Fundamental materials: 8

Ph-BTBT-10

[D5491]

TU-1

[T3922]

TU-3

[T3924]S-DNTT-10

[D5796]

Ph-BTBT-4

[B6248]

Ph-BTBT-6

[H1769]

Ph-BTBT-8

[O0576]

Ph-BTBT-12

[D5910]

High-performance materials (TCI unique): 8

[60]PCBM

[P2682]

[70]PCBM

[P2683]C70

[F1233]

For a wider product lineup,

we also provide normal

semiconductor products.

(without device tests)

Please access TCI website.

TCI Confidential © 2020 19

Topics

1. Introduction

• Tokyo Chemical Industry (TCI)

• Organic Electronics

2. New attempt for high quality semiconductor products

3. Fabrication and evaluation of OFET devices

“Fundamental materials”

• 「Pentacene」• 「P3HT」

“High-performance materials”

• 「Ph-BTBT-n series」• 「TU-n series」

TCI Confidential © 2020 20

「Pentacene」

TCI Confidential © 2020 21

OFET device fabrication: Pentacene

-Details-

< Vacuum Deposition >

•Deposition rate of Pentacene: 0.1 Å/s (under a pressure of∼10−5 Pa)

•Substrate temperature during deposition: RT

•Deposition rate of Au: 0.3 Å/s, (under a pressure of ∼10−4 Pa)

< Device Configuration >

•[n+-Si/SiO2 (200 nm) / Pentacene (60 nm) / Au (60 nm)]

Channel length

50 m

Pentacene-based transistor device

Channel width

1.5 mm

Drain

pentacene

Insulator (SiO2)

Gate (n+-Si)

Source

②pentacene

Insulator (SiO2)

Gate (n+-Si)Vacuum deposition of

pentacene

on the Si/SiO2 substrate

Vacuum deposition of

Au

on the pentacene

Making a semiconductor layer Making electrodes

Insulator (SiO2)

Gate (n+-Si)

n+-Si/SiO2 substrate

①

TCI Confidential © 2020 22

Comparison with other companies’ sublimed pentacene

All pentacene are sublimation grade (High-pure reagent)

Clear difference in transistor performance (electrical property)

We can offer real “usable material”

Mobility: > 0.35 cm2/vs(bare Si/SiO2 substrate)

TCI Confidential © 2020 23

Poor quality pentacene

• Difficult to take “edge-on”

• Not suitable for current flows

Good quality pentacene

• Easy to take “edge-on”

• Suitable for current flows

Images of molecular arrangement

TCI Confidential © 2020 24

Topics

1. Introduction

• Tokyo Chemical Industry (TCI)

• Organic Electronics

2. New attempt for high quality semiconductor products

3. Fabrication and evaluation of OFET devices

“Fundamental materials”

• 「Pentacene」• 「P3HT」

“High-performance materials”

• 「Ph-BTBT-n series」• 「TU-n series」

TCI Confidential © 2020 25

「P3HT」

TCI Confidential © 2020 26

OFET device fabrication: P3HT

Details

< Spin-Coating >

• P3HT 10 mg/ml, 1,2,4-Trichlorobenzene:Chloroform (2:98) mixed solvent

•Spin-coating condition: 1500 RPM, 60 sec, N2

< Vacuum Deposition >

•Deposition rate of Au: 0.2 Å/s (under a pressure of∼10−4 Pa)

< Post-Annealing Treatment >

•Annealing condition: 100 ºC, 30 min, N2

< Device Configuration >

•[n+-Si/SiO (300 nm) / P3HT (100 nm) / Au (40 nm)]

Drain

P3HT

Source

P3HT

Spin-coating of

P3HT

on the Si/SiO2 substrate

Vacuum deposition of

Au

on the P3HT

Making a semiconductor layer Making electrodes

Insulator (SiO2)

Gate (n+-Si)

n+-Si/SiO2 substrate

②①

Channel length

50 m

P3HT-based transistor device

Channel width

1.5 mm

Insulator (SiO2)

Gate (n+-Si)Insulator (SiO2)

Gate (n+-Si)

TCI Confidential © 2020 27

Comparison with other companies’P3HT

Clear difference in transistor performance (electrical property)

“Mobility(electrical property)” highly dependents on its “Regioregularity (RR)”

We can offer real “usable material”

Mobility: > 0.10 cm2/vs(OTS Si/SiO2 substrate)

TCI Confidential © 2020 28

Topics

1. Introduction

• Tokyo Chemical Industry (TCI)

• Organic Electronics

2. New attempt for high quality semiconductor products

3. Fabrication and evaluation of OFET devices

“Fundamental materials”

• 「Pentacene」• 「P3HT」

“High-performance materials”

• 「Ph-BTBT-n series」• 「TU-n series」

TCI Confidential © 2020 29

Ph-BTBT-10, a liquid crystalline material, has

been reported by H. Iino et al.1)

Ph-BTBT-10 exhibited an ultra-high mobility

of 11 cm2/Vs via spin-coting method.1)

1) H. Iino, T. Usui, J. Hanna, Nat. Commun. 2015, 6, 6828.

「Ph-BTBT-n series」

TCI Confidential © 2020 30

OFET device fabrication: Ph-BTBT-10

Details

< Vacuum Deposition>

•Deposition rate of Ph-BTBT-10 0.1 Å/s (under a pressure of∼10−5

Pa)

•Substrate temperature during deposition: 60 °C

•Deposition rate of Au: 0.2 Å/s (under a pressure of∼10−5 Pa)

< Post-Annealing Treatment>

•Annealing condition: 120 ºC, 5 min, N2

< Device configuration>

•[n+-Si/SiO2 (200 nm) / Ph-BTBT-10 (40 nm) / Au (40 nm)]

Drain

Ph-BTBT-10

Insulator

Gate

Source

②Ph-BTBT-10

Insulator (SiO2)

Gate (n+-Si)Vacuum deposition of

Ph-BTBT-10

on the Si/SiO2 substrate

Vacuum deposition of

Au

on the pentacene

Making a semiconductor layer Making electrodes

Insulator (SiO2)

Gate (n+-Si)

n+-Si/SiO2 substrate

①

Channel length

50 m

Ph-BTBT-10-based transistor device

Channel width

1.5 mm

TCI Confidential © 2020 31

Comparison with typical transistor materials

compound Ph-BTBT-10 C8-BTBT DNTT

structure

mobility 11 4.2 0.74

Applicable to both dry and wet processes

Clear difference in transistor performance (electrical property)

Ph-BTBT-10 showed the most excellent OFET performance

Mobility: > 10.0 cm2/vs(ODTS Si/SiO2 substrate)

TCI Confidential © 2020 32

Ph-BTBT-4

[B6248]

New!

Ph-BTBT-6

[H1769]

New!

Ph-BTBT-8

[O0576]

New!

Ph-BTBT-10

[D5491]Ph-BTBT-12

[D5910]

New!

Comparison of mobilities

0.1

1

10

2 4 6 8 10 12 14

Mobili

ty /

cm

2/V

s

Alkyl chain length : -CnH2n+1

Si/SiO2 bare substrates

Vacuum

deposition

Solubility in organic solvents

0

10

20

30

40

50

2 4 6 8 10 12 14

Solu

bili

ty /

mm

ol/L

Alkyl chain length: -CnH2n+1

cyclohexane

toluene

p-xylene

chloroform

chlorobenzene

High mobility / High solubility p-type Organic Semiconductor: “Ph-BTBT-n Series”

TCI Confidential © 2020 33

Ph-BTBT-4

[B6248]

New!

Ph-BTBT-6

[H1769]

New!

Ph-BTBT-8

[O0576]

New!

Ph-BTBT-10

[D5491]Ph-BTBT-12

[D5910]

New!

High mobility / High solubility p-type Organic Semiconductor: “Ph-BTBT-n Series”

Advantages

• “Mobility” and “Solubility” highly depend on the alkyl chain length

• Material choice according to user’s purpose and operating environment

• Applicable to both dry and wet processes

TCI Confidential © 2020 34

Topics

1. Introduction

• Tokyo Chemical Industry (TCI)

• Organic Electronics

2. New attempt for high quality semiconductor products

3. Fabrication and evaluation of OFET devices

“Fundamental materials”

• 「Pentacene」• 「P3HT」

“High-performance materials”

• 「Ph-BTBT-n series」• 「TU-n series」

TCI Confidential © 2020 35

「TU-n series」

Vacuum

deposited

methodSpin-coating

method

TCI Confidential © 2020 36

OFET device fabrication: TU-1

Details

< Vacuum Deposition>

•Deposition rate of TU-1 0.1 Å/s (under a pressure of∼10−5 Pa)

•Substrate temperature during deposition: 60 °C

•Deposition rate of Au: 0.2 Å/s (under a pressure of∼10−5 Pa)

< Post-Annealing Treatment>

•Annealing condition: 150 ºC, 30 min, N2

< Device configuration>

•[n+-Si/SiO2 (200 nm) / TU-1 (40 nm) / Au (40 nm)]

Drain

TU-1

Insulator (SiO2)

Gate (n+-Si)

Source

②TU-1

Insulator (SiO2)

Gate (n+-Si)Vacuum deposition of

TU-1

on the Si/SiO2 substrate

Vacuum deposition of

Au

on the TU-1

Making a semiconductor layer Making electrodes

Insulator (SiO2)

Gate (n+-Si)

n+-Si/SiO2 substrate

①

TU-1

Channel length

50 m

Channel width

1.5 mm

TCI Confidential © 2020 37

OFET device fabrication: TU-3

Details

< Spin-Coating >

• TU-3 0.1wt% in chloroform

•Spin-coating condition: 1000 RPM, N2

< Vacuum Deposition >

•Deposition rate of Au: 0.2 Å/s (under a pressure of∼10−4 Pa)

< Post-Annealing Treatment >

•Annealing condition: 180 ºC, 30 min, N2

< Device Configuration >

•[n+-Si/SiO (200 nm) / TU-3 (20 nm) / Au (40 nm)]

Drain

TU-3

Source

TU-3

Spin-coating of

TU-3

on the Si/SiO2 substrate

Vacuum deposition of

Au

on the TU-3

Making a semiconductor layer Making electrodes

Insulator (SiO2)

Gate (n+-Si)

n+-Si/SiO2 substrate

②①

Insulator (SiO2)

Gate (n+-Si)Insulator (SiO2)

Gate (n+-Si)

TU-3

Channel length

50 m

Channel width

1.5 mm

TCI Confidential © 2020 38

OFET device performance: TU-1 and TU-3

TU-1

[T3922]

TU-3

[T3924]

OR

TU-1

[T3922]

TU-3

[T3924]

compound TU-1 TU-3

Fabrication

method

Vacuum

depositionSpin-coating

Mobility

(cm2/vs)1.2 1.3

Applicable to both dry and/or wet processes

High performance n-type semiconductor materials

Mobility: > 1.0 cm2/vs

TCI Confidential © 2020 39

Summary

TCI Confidential © 2020 40

“New” Organic Transistor Webpage

Articles about product

introduction, device

assessment and

collaboration with

academia and industry.

Details of device

fabrication methods and

device characteristics.

(including other than

HQOS products)

Data list of physical

properties for our

products (e.g. UV-Vis

spectra and 2D-GIXD).

About High-Quality

Organic Semiconductors

(HQOS).

Since Jul. 2020

https://www.tcichemicals.com/IN/en/product/organic-electronics/organic-transistor/index

TCI Confidential © 2020 41

Tokyo Chemical Industry

"Serving Society through Chemical Reagents"