147-14-8

Basic information

• Product Name: (29H,31H-phthalocyaninato(2-)-N29,N30,N31,N32)copper
• Synonyms: Copper, [29H,31H-phthalocyaninato(2-)-N29,N30,N31,N32]-, (SP-4-1)- Copper, [phthalocyaninato(2-)]-;phthalocyanine blueB15:0;Pigment Blue 15 (purified by sublimation);Copper(II) Phthalocyanine (alpha-form);Copper(II) Phthalocyanine (beta-form);Copper(II) phthalocyanine,CuPc, Phthalocyanine blue, Pigment Blue 15;Phthalocyanine Copper(II);CuPC , Copper phthalocyanine
• CAS NO: 147-14-8
• Molecular Formula: C₃₂H₁₆N₈*Cu
• Molecular Weight: 576.07
• EINECS: 205-685-1
• Product Categories: oled materials;Dyes and Pigments;INORGANIC & ORGANIC CHEMICALS;Organometallics;electronic;Classes of Metal Compounds;Cu (Copper) Compounds;Functional Materials;Phthalocyanines;Phthalonitriles & Naphthalonitriles;Transition Metal Compounds;Electroluminescence;Blue needle crystal
• Mol File: 147-14-8.mol
• Article Data: 117

Chemical Properties

• Melting Point: 600°C (dec.)
• Appearance: Dark blue/Fine Crystalline Powder
• Density: 1.62[at 20℃]
• Storage Temp.: Inert atmosphere,Room Temperature
• Water Solubility: <0.1 g/100 mL at 20℃
• Merck: 14,2520
• BRN: 4121848
• CAS DataBase Reference: (29H,31H-phthalocyaninato(2-)-N29,N30,N31,N32)copper(CAS DataBase Reference)
• NIST Chemistry Reference: (29H,31H-phthalocyaninato(2-)-N29,N30,N31,N32)copper(147-14-8)
• EPA Substance Registry System: (29H,31H-phthalocyaninato(2-)-N29,N30,N31,N32)copper(147-14-8)

Safety Data

• Safety Statements: 22-24/25
• RTECS: GL8510000
• TSCA: Yes
• Hazardous Substances Data: 147-14-8(Hazardous Substances Data)

Usage

Description

Copper(II) phthalocyanine, known as CuPc, has been used as an electron donor?with fullerene-C60 or phenyl-C61-butyric acid methyl ester (PCBM) in vacuum-deposited organic photovoltaics (OPV).?Power conversion efficiency of about 1% has been achieved [2] and improved efficiency of 4% with pentacene-doped CuPc layer . CuPc has also been used as a hole-injection material for light-emitting diodes. It has been reported that a thin CuPc layer may effectively enhance the hole injection from the anode to the emissive-polymer layer, resulting in a dramatic decrease of operating voltage of the device . Device stability was achieved by?depositing a copper phthalocyanine CuPc hole-injection layer?HIL on the ITO anode.

Chemical Properties

dark blue fine crystalline powder

Uses

Copper(II) phthalocyanine are involved in the study of photosensitizer chemistry for uniform polymerization, luminescence chemistry and spectrophotometric analysis, organic synthesis and polymerization. This pigment is used in enamels, linoleum, inks, plastics, and rubber goods. Photoisomerizable phthalocyanines are used in rewritable CD or DVD printing.Other applications in organic solar cells, biosensitizers and display devices such as OLED , OTFT, Wearable Display, and e-paper.

Application

Copper(II) phthalocyanine, known as CuPc, has been used as an electron donor with fullerene-C60 or phenyl-C61-butyric acid methyl ester (PCBM) in vacuum-deposited organic photovoltaics (OPV). Power conversion efficiency of about 1% has been achieved [2] and improved efficiency of 4% with pentacene-doped CuPc layer.CuPc has also been used as a hole-injection material for light-emitting diodes. It has been reported that a thin CuPc layer may effectively enhance the hole injection from the anode to the emissive-polymer layer, resulting in a dramatic decrease of operating voltage of the device. Device stability was achieved by depositing a copper phthalocyanine CuPc hole-injection layer HIL on the ITO anode. The improved stability could be contributed to the good match of its highest-occupied molecular orbital (HOMO) level to the work function of ITO, and the improved wetting property of organic materials on ITO. Moreover, CuPc has very weak absorption of light, with wavelengths from 400 to 500 nm, making it suitable for use in blue and green OLEDs.Effective electron-blocking was also observed for inorganic–organic hybrid perovskite solar cells when CuPc-doped spiro-OMeTAD was used as the hole-transporting layer.

General Description

Copper(II) phthalocynaine (CuPc) is a metal phthalocyanine dye that acts as a p-type semiconductor. It has a charge mobility of 10-4 cm2/Vs. It forms a chemically stable thin film that exhibits photoconductivity and catalytic activity.

Flammability and Explosibility

Notclassified

Purification Methods

Precipitate it twice from conc H2SO4 by slow dilution with water. It has also been purified by two or three sublimations at 580o in an argon flow at 300-400Pa. [Beilstein 26 III/IV 4256.]

Properties and Applications

TEST ITEMS SPECIFICATION APPEARANCE BLUE POWDER SHADE REDDISH HEAT RESISTANCE 300 °C min LIGHT FASTNESS 7-8 ACID RESISTANCE 5 ALKALI RESISTANCE 5 FASTNESS TO BLEEDING 5 OIL ABSORPTION 40-45% SPECIFIC SURFACE 29 m 2 /g DENSITY 1.60 g/cm 3 RESIDUE ON 80 MESH 5.0% max WATER SOLUBLE 1.0% max VOLATITE 105 °C 1.0% max TINTING STRENGTH 100-105 %

TEST ITEMS

SPECIFICATION

APPEARANCE

BLUE POWDER

SHADE

REDDISH

HEAT RESISTANCE

300 °C min

LIGHT FASTNESS

7-8

ACID RESISTANCE

5

ALKALI RESISTANCE

5

FASTNESS TO BLEEDING

5

OIL ABSORPTION

40-45%

SPECIFIC SURFACE

29 m 2 /g

DENSITY

1.60 g/cm 3

RESIDUE ON 80 MESH

5.0% max

WATER SOLUBLE

1.0% max

VOLATITE 105 °C

1.0% max

TINTING STRENGTH

100-105 %

InChI:InChI=1/C32H16N8.Cu/c1-2-10-18-17(9-1)25-33-26(18)38-28-21-13-5-6-14-22(21)30(35-28)40-32-24-16-8-7-15-23(24)31(36-32)39-29-20-12-4-3-11-19(20)27(34-29)37-25;/h1-16H;/q-2;

Synthetic route

phthalonitrile (91-15-6) → copper phthalocyanine (147-14-8)

Conditions	Yield
With CuCl2*2H2O for 0.166667h; microwave irradiation;	98%
With CuCl2*2H2O at 190 - 210℃; for 0.25h; microwave irradiation;	88%
With copper diacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene at 140℃; for 0.0833333h;	76%
With 1,1,1,3,3,3-hexamethyl-disilazane; copper(ll) bromide In N,N-dimethyl-formamide at 100℃; for 10h;	74%

phthalic anhydride (85-44-9) → copper phthalocyanine (147-14-8)

Conditions	Yield
With ammonium molybdate tetrahydrate; urea for 0.0833333h; microwave irradiation;	93%
With ammonium molybdate; urea at 200℃; for 0.166667h; microwave irradiation;	80%
Stage #1: phthalic anhydride With N,N-dimethyl-formamide; 1,1,1,3,3,3-hexamethyl-disilazane; copper dichloride; toluene-4-sulfonic acid at 150℃; for 10h; Stage #2: With sulfuric acid	62%

phthalimide (136918-14-4) → copper phthalocyanine (147-14-8)

Conditions	Yield
Stage #1: phthalimide With toluene-4-sulfonic acid; 1,1,1,3,3,3-hexamethyl-disilazane; copper(ll) bromide; N,N-dimethyl-formamide at 150℃; for 10h; Stage #2: With sulfuric acid	72%

copper phthalocyanine (147-14-8) → copper ftalocyanine tetra-3-sulfonyl chloride

Conditions	Yield
With chlorosulfonic acid; thionyl chloride 1.) 138 - 140 deg C, 3 h, 2.) 80 - 85 deg C, 3 h; Multistep reaction;

Upstream product

• 10125-13-0 Copper(II) chloride dihydrate 
• 557-05-1 Zinc stearate 
• 57-13-6 Urea 
• 12054-85-2 Ammonium molybdate tetrahydrate 
• 13106-76-8 AMMONIUM MOLYBDATE 
• 1330-20-7 Xylene 
• 85-44-9 Phthalic anhydride 
• 13933-17-0 Copper(II) chloride dihydrate 
• 7681-11-0 Potassium iodide 
• 7758-89-6 Cuprous chloride 
• 8014-95-7 SULFURIC ACID 

Downstream Products

• 12236-85-0 Reactive Blue 14 
• 1328-53-6 Pigment Geen 7 
• 1330-38-7 Direct Blue 86 
• 12227-06-4 Sulphur Green 14 
• 12236-86-1 Reactive Turquoise Blue Kn-G 
• 12222-04-7 Direct Blue 199 
• 1308-38-9 Chromium oxide 
• 115682-09-2 Reactive Blue 231 
• 25135-51-7 POLYSULFONE 

Recommend Products

• 88-99-3  benzene-1,2-dicarboxylic acid 
• 7789-45-9  copper(ll) bromide 
• 25248-76-4  29H,31H-phthalocyanine 
• 160956-25-2  isoindole-1,3-diylidenediamine 
• 85-44-9  phthalic anhydride 
• 57-13-6  urea 
• 91-15-6  phthalonitrile 
• 7681-65-4  copper(l) iodide 
• 12775-96-1  copper 
• 184303-72-8  phthalanhydride 
• 10027-30-2  copper(II) phthalate 
• 88-95-9  Phthaloyl dichloride 
• 17174-98-0  o-cyanobenzamide