# US 8,772,767 B2 · Organic light-emitting diode luminaires

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- Number: US 8,772,767 B2
- Document ID: US8772767B2
- Status: Granted
- Kind: B2
- Application number: 13/900,130
- Filed: 2013-05-22
- Published: 2013-10-03
- Granted: 2014-07-08
- Earliest claimed: 2009-08-24
- Assignees: E. I. Du Pont de Nemours and Company
- Applicants: E I du Pont de Nemours and Company
- Inventors: Kerwin D Dobbs; Norman Herron; Vsevolod Rostovtsev
- Web page: https://patentgrep.com/patent/US8772767B2

## CPC

- C09K 11/06: containing organic luminescent materials
- C09B 57/00: Other synthetic dyes of known constitution
- C09B 57/10: Metal complexes of organic compounds not being dyes in uncomplexed form
- H05B 33/14: characterised by the chemical or physical composition or the arrangement of the electroluminescent material {, or by the simultaneous addition of the electroluminescent material in or onto the light source}
- H10K 59/35: comprising red-green-blue [RGB] subpixels
- H10K 59/352: {the areas of the RGB subpixels being different}
- H10K 71/12: using liquid deposition, e.g. spin coating
- C09K 2211/1007: Non-condensed systems
- C09K 2211/1011: Condensed systems
- C09K 2211/1029: containing one nitrogen atom as the heteroatom
- C09K 2211/1044: containing two nitrogen atoms as heteroatoms
- C09K 2211/185: of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
- H10K 59/877: {comprising scattering means}
- H10K 59/879: {comprising refractive means, e.g. lenses}
- H10K 85/342: {comprising iridium}
- H10K 85/633: {comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom}
- Y02B 20/00: Energy efficient lighting technologies, e.g. halogen lamps or gas discharge lamps
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- 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)
- H05B: ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- Y02B: CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO BUILDINGS, e.g. HOUSING, HOUSE APPLIANCES OR RELATED END-USER APPLICATIONS

## Abstract

There is provided an organic light-emitting diode luminaire. The luminaire includes a patterned first electrode, a second electrode, and a light-emitting layer therebetween. The light-emitting layer includes a first plurality of pixels having an emission color that is blue; a second plurality of pixels having an emission color that is green, the second plurality of pixels being laterally spaced from the first plurality of pixels; and a third plurality of pixels having an emission color that is red-orange, the third plurality of pixels being laterally spaced from the first and second pluralities of pixels. The additive mixing of all the emitted colors results in an overall emission of white light.

## Claims

### Claim 1

A process for making an OLED luminaire, comprising:
providing a substrate having a first patterned electrode thereon;
depositing a first liquid composition in a first pixellated pattern to form a first deposited composition, the first liquid composition comprising a first electroluminescent material in a first liquid medium, said first electroluminescent material having a first emission color;
depositing a second liquid composition in a second pixellated pattern which is laterally spaced from the first pixellated pattern to form a second deposited composition, the second liquid composition comprising a second electroluminescent material in a second liquid medium, said second electroluminescent material having a second emission color;
depositing a third liquid composition in a third pixellated pattern which is laterally spaced from the first and second pixellated patterns to form a third deposited composition, the third liquid composition comprising a third electroluminescent material in a third liquid medium, said third electroluminescent material having a third emission color;
drying the deposited compositions to form pluralities of pixels; and
forming a second electrode over all the pixels;
wherein one of the emission colors is blue, one of the emission colors is green, and one of the emission colors is red-orange; wherein the electroluminescent material with blue emission color has Formula I
wherein: R14, R15, R16 and R17 are the same or different and are selected from the group consisting of H, D, and alkyl, where R14 and R15 groups or R16 and R17 groups may be joined together to form a 5- or 6-membered aliphatic ring; R18 and R19 are the same or different and are selected from the group consisting of D, alkyl groups, silyl groups, m-phenyl, o-phenyl, p-phenyl, m-N-carbazolyl, and p-N-carbazolyl; R20 is the same or different at each occurrence and is selected from the group consisting of D, alkyl groups, silyl groups, phenyl, and biphenyl, or two adjacent R20 groups can join together to form a naphthyl or fluorenyl group; a and b are the same or different and are an integer from 0-10; c and d are the same or different and are an integer from 1-5; f, g, h, and i, are the same or different at each occurrence and are an integer from 0-4; and e and j are the same or different at each occurrence and are an integer from 0-5.

### Claim 2 (depends on 1)

The process of claim 1, wherein the electroluminescent material with blue emission color is a tris-cyclometallated complex having the formula IrL3 or a bis-cyclometallated complex having the formula IrL2Y, where Y is a monoanionic bidentate ligand and L has a formula selected from the group consisting of Formula L-1 through Formula L-12:
where R1 through R8 are the same or different and are selected from the group consisting of H, D, electron-donating groups, and electron-withdrawing groups, and R9 is H, D, or alkyl;
* represents a point of coordination with Ir.

### Claim 3 (depends on 1)

The process of claim 1, wherein the relative emission from the blue, green and red-orange colors, measured in cd/m2, is:
blue emission=20-25%,
green emission=47-52%, and
red-orange emission=27-32%.

### Claim 4 (depends on 1)

The process of claim 1, wherein the electroluminescent material with green emission color is a tris-cyclometallated complex having the formula IrL3 or a bis-cyclometallated complex having the formula IrL2Y, where Y is a monoanionic bidentate ligand and L has a formula selected from the group consisting of L-1, L-3 through L-7, and L-9 through L-17:
where R1 through R8 are the same or different and are selected from the group consisting of H, D, electron-donating groups, and electron-withdrawing groups, and R9 is H, D, or alkyl.

### Claim 5 (depends on 1)

The process of claim 1, wherein the electroluminescent material with red-orange emission color is a tris-cyclometallated complex having the formula IrL3 or a bis-cyclometallated complex having the formula IrL2Y, where Y is a monoanionic bidentate ligand and L has a formula selected from the group consisting of Formula L-18, L-19, L-20 and L-21:
where:
R1 through R6 and R21 through R30 are the same or different and are selected from the group consisting of H, D, electron-donating groups, and electron-withdrawing groups; AND
* represents a point of coordination with Ir.

### Claim 6 (depends on 1)

The process of claim 1, wherein any one or more of the first, second, and third electroluminescent materials comprise a host material having a formula selected from:
An-L-An
and
A-An-A
wherein An is an anthracene moiety, L is a divalent connecting group, and A is the same or different at each occurrence and is an aromatic group.

### Claim 7 (depends on 1)

The process of claim 1, wherein one or more of the first, second, and third electroluminescent materials comprises a host material having the formula
where:
Ar1 to Ar4 are the same or different and are aryl;
Q is selected from the group consisting of multivalent aryl groups and
T is selected from the group consisting of (CR′)a, SiR2, S, SO2, PR, PO, PO2, BR, and R;
R is the same or different at each occurrence and is selected from the group consisting of alkyl, and aryl;
R′ is the same or different at each occurrence and is selected from the group consisting of H, D, and alkyl;
a is an integer from 1-6; and
m is an integer from 0-6.

### Claim 8 (depends on 1)

The process of claim 1, wherein one or more of the first, second, and third electroluminescent materials comprise a host material selected from the group consisting of:

### Claim 9 (depends on 1)

The process of claim 1, wherein one or more of the first, second, and third electroluminescent materials comprise a host material having the formula
where:
R31 is the same or different and is selected from the group consisting of phenyl, naphthyl, naphthylphenyl, triphenylamino, and carbazolylphenyl;
R32 and R33 are the same or different and are selected from the group consisting of phenyl, biphenyl, naphthyl, naphthylphenyl, phenanthryl, triphenylamino, and carbazolylphenyl.

### Claim 10 (depends on 2)

The process of claim 2, wherein:
R1 is H, D, F, or alkyl;
R2 is H, D or alkyl;
R3=H, D, F, alkyl, OR10, NR102;
R4=H or D;
R5=H, D or F;
R6=H, D, CN, F, aryl, fluoroalkyl, or diaryloxophosphinyl;
R7=H, D, F, alkyl, aryl, or diaryloxophosphinyl;
R8=H, D, CN, alkyl, fluoroalkyl;
R9=H, D, or alkyl; and
R10=alkyl, where adjacent R10 groups can be joined to form a saturated ring.

### Claim 11 (depends on 2)

The process of claim 2, wherein Y is selected from the group consisting of Y-1, Y-2 and Y-3
wherein:
R11 is the same or different at each occurrence and is selected from the group consisting of alkyl and fluoroalkyl;
R12 is H, D or F; and
R13 is the same or different at each occurrence and is selected from the group consisting of alkyl and fluoroalkyl.

### Claim 12 (depends on 2)

The process of claim 2, wherein the relative emission from blue, green and red-orange colors, as measured in cd/m2, is:
blue emission=28-33%,
green emission=32-37%, and
red-orange emission=31-36%.

### Claim 13 (depends on 4)

The process of claim 4, wherein:
R1=H, D or F;
R2=H, D, F, or alkyl;
R3=H, D or diarylamino;
R4=H, D or F;
R5=H, D or alkyl, or R4 and R5 may be joined together to form a 6-membered aromatic ring;
R6=H, D, CN, F, aryl, fluoroalkoxy, N-carbazolyl, diphenyl-N-carbazolyl
R7=H, D, F, fluoroalkoxy, N-carbazolyl, or diphenyl-N-carbazolyl;
R8=H, D or F; and
R9=H, D, or alkyl,
where the asterisk represents the point of attachment.

### Claim 14 (depends on 4)

The process of claim 4, wherein Y is selected from the group consisting of Y-1, Y-2 and Y-3
wherein:
R11 is the same or different at each occurrence and is selected from the group consisting of alkyl and fluoroalkyl;
R12 is H, D or F; and
R13 is the same or different at each occurrence and is selected from the group consisting of alkyl and fluoroalkyl.

### Claim 15 (depends on 5)

The process of claim 5, wherein:
R1 through R4 and R21 through R26 are the same or different and are H, D, alkyl, silyl, or alkoxy, or R1 and R2, R2 and R3 or R3 and R4 in ligand L-18, or R23 and R24 or R24 and R25 in ligand L-19 and L-20, or R23 and R24, R24 and R25, or R25 and R26 can be joined together to form a hydrocarbon ring or hetero ring;
R27=H, D, alkyl, or silyl;
R28=H, D, alkyl, or silyl;
R29=H, D, alkyl, silyl, alkoxy, fluoroalkoxy, or aryl; and
R30=H, D, alkyl, or silyl.

### Claim 16 (depends on 5)

The process of claim 5, wherein Y is selected from the group consisting of Y-1, Y-2 and Y-3
wherein:
R11 is the same or different at each occurrence and is selected from the group consisting of alkyl and fluoroalkyl;
R12 is H, D or F; and
R13 is the same or different at each occurrence and is selected from the group consisting of alkyl and fluoroalkyl.

### Claim 17 (depends on 6)

The process of claim 6, wherein the host material has the formula
where:
A1 and A2 are the same or different at each occurrence and are selected from the group consisting of H, D, an aromatic group, an alkyl group and an alkenyl group, or A may represent one or more fused aromatic rings;
p and q are the same or different and are an integer from 1-3.