# US 9,040,962 B2 · Depositing premixed materials

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- Number: US 9,040,962 B2
- Document ID: US9040962B2
- Status: Granted
- Kind: B2
- Application number: 13/640,000
- Filed: 2010-04-28
- Published: 2013-05-09
- Granted: 2015-05-26
- Earliest claimed: 2010-04-28
- Assignees: Universal Display Corporation; Nippon Steel & Sumikin Chemical Co., Ltd.
- Applicants: Vadim Adamovich; Michael Weaver; Raymond Kwong; Chuanjun Xia; Bert Alleyne; Takahiro Kai; Masaki Komori; Toshihiro Yamamoto
- Inventors: Vadim Adamovich; Michael Weaver; Raymond Kwong; Chuanjun Xia; Bert Alleyne; Takahiro Kai; Masaki Komori; Toshihiro Yamamoto
- Web page: https://patentgrep.com/patent/US9040962B2

## CPC

- H10K 85/657: {Polycyclic condensed heteroaromatic hydrocarbons}
- C09B 57/00: Other synthetic dyes of known constitution
- H10K 85/622: {containing four rings, e.g. pyrene}
- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- H10K 85/6574: {comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes}
- H10K 85/6576: {comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene}
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 71/30: Doping active layers, e.g. electron transporting layers
- H10K 85/324: {comprising aluminium, e.g. Alq3}
- H10K 85/342: {comprising iridium}
- H10K 2101/90: {Multiple hosts in the emissive layer}
- H10K 2102/103: {comprising indium oxides, e.g. ITO}
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- C09B: ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES {, e.g. PIGMENTS}; MORDANTS; LAKES (fermentation or enzyme using processes to synthesise a desired chemical compound C12P)

## Abstract

A combination of host materials suitable for co-evaporation or premix evaporation, and devices containing the combination of host materials are provided. The combination of host materials provides improved lifetime and efficiency. A method for fabricating devices containing the host material combination is also provided.

## Claims

### Claim 1

A first device comprising an organic light emitting device, further comprising:
a first electrode;
a second electrode; and
a first organic layer, disposed between the first electrode and the second electrode, wherein the first organic layer comprises an organic composition;
wherein the organic composition comprises
a first compound having the formula:
wherein X is S or O;
wherein R1 and R2 are substituents independently selected from the group consisting of CnH2n+1,OCnH2n+1, OAr1, N(CnH2n+1)2, N(Ar1)(Ar2), CH═CH—CnH2n+1, C≡CHCnH2n+1,Ar1, Ar1—Ar2, CnH2n—Ar1, and no substitution;
wherein each of R1 and R2 may represent mono, di, tri, or tetra substitutions;
wherein n is 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10;
wherein Ar1 and Ar2 are independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof; and
wherein at least one of R1 and R2 includes a triphenylene group; and
a second compound having the formula (1):
wherein
Y is an m-valent aromatic hydrocarbon group of 6 to 50 carbon atoms or an m-valent aromatic heterocyclic group of 3 to 50 carbon atoms excluding a group having more than 5 condensed rings;
m denotes an integer of 1 to 3, such that when m is greater than 2, each Z may be the same or different;
Z is represented by formula (1 a):
wherein
ring A is an aromatic hydrocarbon ring represented by formula (1 b)
ring B is a heterocyclic ring represented by formula (1 c)
ring A and B are respectively condensed with the adjacent rings;
R6, R7, and R8 are each independently selected from the group consisting of hydrogen, an aliphatic hydrocarbon group of 1 to 10 carbon atoms, an aromatic hydrocarbon group of 6 to 18 carbon atoms, and an aromatic heterocyclic group of 3 to 17 carbon atoms; and
Ar3 is an aromatic hydrocarbon group of 6 to 50 carbon atoms, or an aromatic heterocyclic group of 3 to 50 carbon atoms excluding a group having more than 5 condensed rings.

### Claim 2 (depends on 1)

The first device of claim 1, wherein the first compound has the formula:
wherein X is S or O;
wherein each of R1, R2, R3, R4, and R5 may represent mono, di, tri, or tetra substitutions;
wherein R1, R2, R3, R4, and R5 are independently selected from the group consisting of hydrogen, halogen, alkyl, alkoxy, amino, alkenyl, alkynyl, aryl and heteroaryl; and
wherein the second compound has the formula (2):
wherein
Y′ is an m-valent aromatic hydrocarbon group of 6 to 40 carbon atoms or an m-valent aromatic heterocyclic group of 3 to 40 carbon atoms excluding a group having more than 5 condensed rings;
m denotes an integer of 1 or 2 , and when m=2, each Z may be the same or different;
Z is represented by formula (2 a):
wherein ring A is an aromatic hydrocarbon ring represented by formula (2 b),
ring B is a heterocyclic ring represented by formula (2 c),
ring A and B are respectively condensed with the adjacent rings;
R6, R7, and R8 are independently selected from the group consisting of hydrogen, an aliphatic hydrocarbon group of 1 to 10 carbon atoms, an aromatic hydrocarbon group of 6 to 18 carbon atoms, and an aromatic heterocyclic group of 3 to 17 carbon atoms; and
Ara′ is an aromatic hydrocarbon group of 6 to 40 carbon atoms, or an aromatic heterocyclic group of 3 to 40 carbon atoms excluding a group having more than 5 condensed rings.

### Claim 3 (depends on 2)

The first device of claim 2, wherein the set of non-hydrogen substituents selected for R1, R2, R3, R4, and R5, and the set of non-hydrogen substituents selected for R6, R7, and R8 are the same.

### Claim 4 (depends on 1)

The first device of claim 1, wherein the first compound has the formula:
wherein X is S or O;
wherein each of R1, R2, R3, R4, and R5 may represent mono, di, tri, or tetra substitutions;
wherein R1, R2, R3, R4, and R5 are independently selected from the group consisting of hydrogen, halogen, alkyl, alkoxy, amino, alkenyl, alkynyl, aryl and heteroaryl; and
wherein the second compound has the formula (3):
wherein
Y″ is a monovalent aromatic heterocyclic group of 3 to 30 carbon atoms excluding a group having more than 5 condensed rings;
m denote an integer of 1;
Z is a represented by formula (3 a), and
wherein
ring A is an aromatic hydrocarbon ring represented by formula (3 b),
ring B is a heterocyclic ring represented by formula (3 c),
ring A and ring B are respectively condensed with the adjacent rings;
R6, R7, and R8 are independently selected from the group consisting of hydrogen, an aliphatic hydrocarbon group of 1 to 10 carbon atoms, an aromatic hydrocarbon group of 6 to 18 carbon atoms, and an aromatic heterocyclic group of 3 to 17 carbon atoms; and
Ara′ is an aromatic hydrocarbon group of 6 to 30 carbon atoms, or an aromatic heterocyclic group of 3 to 30 carbon atoms excluding a group having more than 5 condensed rings.

### Claim 5 (depends on 4)

The first device of claim 4, wherein the first compound is selected from the group consisting of:

### Claim 6 (depends on 5)

The first device of claim 5 wherein the second compound is selected from the group consisting of:

### Claim 7 (depends on 1)

The first device of claim 1, wherein the first compound has the formula:
wherein X is S or O;
wherein each of R1, R2, R3, R4, and R5 may represent mono, di, tri, or tetra substitutions;
wherein R1, R2, R3, R4, and R5 are independently selected from the group consisting of hydrogen, halogen, alkyl, alkoxy, amino, alkenyl, alkynyl, aryl and heteroaryl;
wherein L is selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof; and
wherein the second compound has the formula:
wherein
Y′ is an m-valent aromatic hydrocarbon group of 6 to 40 carbon atoms or an m-valent aromatic heterocyclic group of 3 to 40 carbon atoms excluding a group having more than 5 condensed rings;
m denotes an integer of 1 or 2 , and in the case of m=2, each Z may be the same or different;
Z is represented by formula (2 a)
wherein
ring A is an aromatic hydrocarbon ring represented by formula (2 b)
ring B is a heterocyclic ring represented by formula (2 c)
ring A and B are respectively condensed with the adjacent rings;
R6, R7, and R8 are independently selected from the group consisting of hydrogen, an aliphatic hydrocarbon group of 1 to 10 carbon atoms, an aromatic hydrocarbon group of 6 to 18 carbon atoms, and an aromatic heterocyclic group of 3 to 17 carbon atoms; and
Ara′ is an aromatic hydrocarbon group of 6 to 40 carbon atoms, or an aromatic heterocyclic group of 3 to 40 carbon atoms excluding a group having more than 5 condensed rings.

### Claim 8 (depends on 7)

The first device of claim 7, wherein the set of non-hydrogen substituents selected for R1, R2, R3, R4, and R5, and the set of non-hydrogen substituents selected for R6, R7, and R8 are the same.

### Claim 9 (depends on 1)

The first device of claim 1, wherein the first compound has the formula:
wherein X is S or O;
wherein each of R1, R2, R3, R4, R5, and R6 may represent mono, di, tri, or tetra substitutions;
wherein R1, R2, R3, R4, R5, and R6 are independently selected from the group consisting of hydrogen, halogen, alkyl, alkoxy, amino, alkenyl, alkynyl, aryl and heteroaryl; and
wherein the second compound has the formula:
wherein
Y″ is a monovalent aromatic heterocyclic group of 3 to 30 carbon atoms excluding a group having more than 5 condensed rings;
m denotes an integer of 1;
Z is a represented by formula (3 a),
wherein ring A is an aromatic hydrocarbon ring represented by formula 3 b:
ring B is a heterocyclic ring represented by formula (3 c)
ring A and B are respectively condensed with the adjacent rings;
R6, R7, and R8 are independently selected from the group consisting of hydrogen, an aliphatic hydrocarbon group of 1 to 10 carbon atoms, an aromatic hydrocarbon group of 6 to 18 carbon atoms, and an aromatic heterocyclic group of 3 to 17 carbon atoms; and
Ara′ is an aromatic hydrocarbon group of 6 to 30 carbon atoms, or an aromatic heterocyclic group of 3 to 30 carbon atoms excluding a group having more than 5 condensed rings.

### Claim 10 (depends on 1)

The first device of claim 1, wherein the first compound is selected from the group consisting of:

### Claim 11 (depends on 10)

The first device of claim 10 wherein the second compound is selected from the group consisting of:

### Claim 12 (depends on 1)

The first device of claim 1, wherein the first organic layer is an emissive layer and the first compound and the second compound are hosts, and wherein the emissive layer further comprises an emissive phosphorescent dopant.

### Claim 13 (depends on 1)

The first device of claim 1, wherein the emissive phosphorescent dopant is selected from the group consisting of:

### Claim 14 (depends on 1)

The first device of claim 1, wherein the first electrode is an anode and the first organic layer is deposited over the anode.

### Claim 15 (depends on 1)

The first device of claim 1, wherein the device further comprises a second organic layer different from the first organic layer, and the first organic layer is a non-emissive layer.

### Claim 16 (depends on 15)

The first device of claim 15, wherein the first organic layer is a blocking layer.

### Claim 17 (depends on 1)

The first device of claim 1, wherein the first compound has an evaporation temperature and the second compound has an evaporation temperature, wherein the evaporation temperature of the first compound is within 30° C. of the evaporation temperature of the second compound.

### Claim 18

A method of fabricating an organic light emitting device comprising a first electrode, a second electrode, and a first organic layer disposed between the first electrode and the second electrode, wherein the first organic layer comprises an organic composition further comprising a first compound and a second compound, the method comprising:
providing a substrate having the first electrode disposed thereon;
depositing the organic composition over the first electrode; and
depositing the second electrode over the first organic layer,
wherein the first compound has the formula:
wherein X is S or O;
wherein R1 and R2 are substituents independently selected from the group consisting of CnH2n+1,O CnH2n+1, OAr1, N(CnH2n+1)2, N(Ar1)(Ar2), CH═CH—CnH2n+1, C≡CHCnH2n+1,Ar1, Ar1—Ar2, CnH2n—Ar1, and no substitution;
wherein n is 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10;
wherein Ar1 and Ar2 are independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof; and
wherein at least one of R1 and R2 includes a triphenylene group; and
wherein the second compound has the formula (1)
wherein
Y is an m-valent aromatic hydrocarbon group of 6 to 50 carbon atoms or an m-valent aromatic heterocyclic group of 3 to 50 carbon atoms excluding a group having more than 5 condensed rings;
m denotes an integer of 1 to 3, such that when m is greater than 2, each Z may be the same or different;
Z is represented by formula (1 a):
wherein
ring A is an aromatic hydrocarbon ring represented by formula (1 b)
ring B is a heterocyclic ring represented by formula (1 c)
ring A and ring B are respectively condensed with the adjacent rings;
R6, R7, and R8 are each independently selected from the group consisting of hydrogen, an aliphatic hydrocarbon group of 1 to 10 carbon atoms, an aromatic hydrocarbon group of 6 to 18 carbon atoms, and an aromatic heterocyclic group of 3 to 17 carbon atoms; and,
Ar3 is an aromatic hydrocarbon group of 6 to 50 carbon atoms, or an aromatic heterocyclic group of 3 to 50 carbon atoms excluding a group having more than 5 condensed rings.

### Claim 19

A host composition comprising a mixture of a first compound and a second compound, wherein the first compound has the formula:
wherein X is S or O;
wherein each of R1, R2, R3, R4, and R5 may represent mono, di, tri, or tetra substitutions;
wherein R1, R2, R3, R4, and R5 are independently selected from the group consisting of hydrogen, halogen, alkyl, alkoxy, amino, alkenyl, alkynyl, aryl and heteroaryl; and
wherein the second compound has the formula (2):
wherein
Y′ is an m-valent aromatic hydrocarbon group of 6 to 40 carbon atoms or an m-valent aromatic heterocyclic group of 3 to 40 carbon atoms excluding a group having more than 5 condensed rings;
m denotes an integer of 1 or 2 , and when m=2, each Z may be the same or different;
Z is represented by formula (2 a):
wherein ring A is an aromatic hydrocarbon ring represented by formula (2 b),
ring B is a heterocyclic ring represented by formula (2 c),
ring A and ring B are respectively condensed with the adjacent rings;
R6, R7, and R8 are independently selected from the group consisting of hydrogen, an aliphatic hydrocarbon group of 1 to 10 carbon atoms, an aromatic hydrocarbon group of 6 to 18 carbon atoms, and an aromatic heterocyclic group of 3 to 17 carbon atoms; and
Ara′ is an aromatic hydrocarbon group of 6 to 40 carbon atoms, or an aromatic heterocyclic group of 3 to 40 carbon atoms excluding a group having more than 5 condensed rings.

### Claim 20

A host composition comprising a mixture of a first compound and a second compound, wherein the first compound has the formula:
wherein X is S or O;
wherein each of R1, R2, R3, R4, and R5 may represent mono, di, tri, or tetra substitutions;
wherein R1, R2, R3, R4, and R5 are independently selected from the group consisting of hydrogen, halogen, alkyl, alkoxy, amino, alkenyl, alkynyl, aryl and heteroaryl;
wherein L is selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof; and
wherein the second compound has the formula:
wherein
Y′ is an m-valent aromatic hydrocarbon group of 6 to 40 carbon atoms or an m-valent aromatic heterocyclic group of 3 to 40 carbon atoms excluding a group having more than 5 condensed rings;
m denotes an integer of 1 or 2 , and when m=2, each Z may be the same or different;
Z is represented by formula (2 a):
wherein ring A is an aromatic hydrocarbon ring represented by formula (2 b),
ring B is an heterocyclic ring represented by formula (2 c),
ring A and ring B are respectively condensed with the adjacent rings;
R6, R7, and R8 are independently selected from the group consisting of hydrogen, an aliphatic hydrocarbon group of 1 to 10 carbon atoms, an aromatic hydrocarbon group of 6 to 18 carbon atoms, and an aromatic heterocyclic group of 3 to 17 carbon atoms; and
Ara′ is an aromatic hydrocarbon group of 6 to 40 carbon atoms, or an aromatic heterocyclic group of 3 to 40 carbon atoms excluding a group having more than 5 condensed rings.