IP Library › Granted Patent US 11,690,285
Granted Patent B2
US 11,690,285 · App. 17/328,403 · Granted Jun 27, 2023

Electroluminescent devices

Inventors: Nicholas J. Thompson (New Hope, PA); Chun Lin (Yardley, PA); Hsiao-Fan Chen (Lawrence Township, NJ)
Assignee: UNIVERSAL DISPLAY CORPORATION
H01L51/0087C07D403/14C07F5/027C07F7/0812C07F15/0086C09K11/06H01L51/008H01L51/0067H01L51/0071H01L51/0072H01L51/0094C07B2200/05C09K2211/1018C09K2211/1048C09K2211/185H01L51/5016H01L2251/5384H01L2251/552
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Quick Facts
Patent No.
US 11,690,285
App. No.
17/328,403
Granted
Jun 27, 2023
Kind
B2
Abstract

Disclosed is an OLED configuration that although comprises an exciplex that has an emission spectrum that is redder than the emission spectrum of the emitter, the emission from the exciplex is suppressed so that the overall OLED emission spectrum is still dominated by the emission of the emitter.

Claims (158)

1. An organic light emitting device (OLED) having an emission spectrum, the OLED comprising:

an anode;

a cathode; and

an organic emissive layer, disposed between the anode and the cathode, comprising:

a first host material having a highest occupied molecular orbital (HOMO) energy and a lowest unoccupied molecular orbital (LUMO) energy; and

an emitter material having a HOMO energy and a LUMO energy;

wherein,

all materials in the organic emissive layer are mixed together;

the emitter material is a phosphorescent metal complex;

High HOMO energy is the highest HOMO energy among all materials in the organic emissive layer;

Low LUMO energy is the lowest LUMO energy among all materials in the organic emissive layer;

a≤E T −ΔE≤b, wherein E T is triplet energy T 1 of the emitter material, which is the lowest T 1 energy among all materials in the organic emissive layer, ΔE is the energy gap between the High HOMO energy and the Low LUMO energy, a is 0.00 up to 0.15 eV, and b is 0.05 up to 0.45 eV; and

wherein root mean squared function (RMSD) value for the emission spectrum of the OLED and an emission spectrum of a reference OLED, whose organic emissive layer consists of the emitter material and an inert host, is not greater than 0.05,

wherein RMSD value is a single value that represents the average difference between the emission spectrum of the OLED and the emission spectrum of the reference OLED at all wavelengths obtained by the following equation:

R

⁢

M

⁢

S

⁢

D

=

1

n

⁢

∑

1

n

(

I

1

(

λ

)

-

I

2

(

λ

)

)

2

,

wherein n is the number of points on the two emission spectrums being compared, and I 1 and I 2 are the normalized intensity spectrums as a function of wavelength, λ.

2. The OLED of claim 1 , wherein E T is at least 2.60 eV.

3. The OLED of claim 1 , wherein the High HOMO energy is the HOMO energy of the emitter material, and the Low LUMO energy is the LUMO energy of the first host.

4. The OLED of claim 1 , wherein the High HOMO energy is the HOMO energy of the first host, and the Low LUMO energy is the LUMO energy of the emitter material.

5. The OLED of claim 1 , wherein the OLED further comprises a second host, wherein the High HOMO energy is the HOMO energy of the first host, and the Low LUMO energy is the LUMO energy of the second host.

6. The OLED of claim 1 , wherein the OLED further comprises a second host, wherein the High HOMO energy is the HOMO energy of the second host, and the Low LUMO energy is the LUMO energy of the first host.

7. The OLED of claim 1 , wherein the first host comprises at least one chemical moiety selected from the group consisting of triphenylene, carbazole, indolocarbazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, pyridine, pyridazine, pyrimidine, pyrazine, triazine, imidazole, boryl, 5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene, and aza-variants thereof.

8. The OLED of claim 1 , wherein the emitter material has the formula of M(L 1 ) x (L 2 ) y (L 3 ) z ;

wherein,

L 1 , L 2 and L 3 can be the same or different;

x is 1, 2, or 3;

y is 0, 1, or 2;

z is 0, 1, or 2;

x+y+z is the oxidation state of the metal M;

L 1 , L 2 , and L 3 are each independently selected from the group consisting of:

wherein;

T is selected from the group consisting of B, Al, Ga, and In;

each Y 1 to Y 13 are independently selected from the group consisting of carbon and nitrogen;

Y′ is selected from the group consisting of BR e , NR e , PR e , O, S, Se, C═O, S═O, SO 2 , CR e R f , SiR e R f , and GeR e R f ;

R e and R f can be fused or joined to form a ring;

each R a , R b , R e , and R d may represent from mono substitution to the possible maximum number of substitution, or no substitution;

each of the R a1 , R b1 , R c1 , R d1 , R a , R b , R c , R d , R e and R f is independently a hydrogen or a substituent selected from the group consisting of deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, boryl, selenyl, and combinations thereof; and

any two R a1 , R b1 , R c1 , R d1 , R a , R b , R c , R d , R e and R f can be fused or joined to form a ring or form a multidentate ligand.

9. The OLED of claim 8 , wherein at least one of R a1 , R b1 , R c1 , R d1 , R a , R b , R c , R d , R e and R f comprises a chemical group containing at least three 6-membered aromatic rings that are not fused next to each other.

10. The OLED of claim 8 , wherein the emitter material has the formula selected from the group consisting of Pt(L 1 ) 2 , Pt(L 1 )(L 2 ), Pd(L 1 ) 2 , and Pd(L 1 )(L 2 ); wherein L 1 and L 2 are each a different bidentate ligand; and wherein L 1 can be connected to the other L 1 or L 2 to form a tetradentate ligand.

11. The OLED of claim 8 , wherein the emitter material comprises at least one metal-carbene bond.

12. The OLED of claim 8 , wherein the minimum amount of the hydrogen of the emitter material being deuterated is selected from the group consisting of 25%, 30%, 35%, 40%, 50%, 60%, 70%, 80%, 90%, and 100%.

13. The OLED of claim 10 , wherein the emitter material is selected from the group consisting of:

wherein,

X 1 to X 20 is C or N;

L a is selected from the group consisting of O, S, Se, NR, PR, BR, BRR′, CRR′, SiRR′, GeRR′, and C═X, wherein X is O, S, NR″, or CR′R″;

each R, R′, R″, R A to R F represents from mono substitution to the possible maximum number of substitutions, or no substitution;

each R, R′, R″, R A to R F is independently a hydrogen or a substitution selected from the group consisting of deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, boryl, selenyl, and combinations thereof; and

any two R, R′, R″, R A to R F are optionally fused or joined to form a ring or form a multidentate ligand.

14. The OLED of claim 13 , wherein at least one of R A to R F comprises a chemical group containing at least three 6-membered aromatic rings that are not fused next to each other.

15. The OLED of claim 13 , wherein R A comprises a chemical group containing at least three 6-membered aromatic rings that are not fused next to each other.

16. The OLED of claim 13 , wherein the emitter material is selected from the group consisting of:

17. The OLED of claim 13 , wherein the emitter material is selected from the group consisting of the structures defined by β-(Ri)(Rj)(Rk)(Rl)(Rm)(Rn), where β is an integer from 1 to 15, and β′-(Ri)(Rj)(Rk)(Rl)(Rm)(Rn)(Xo), where β′ is an integer from 16 to 27, where i is an integer from 1 to 292, j, k, l, m, and n are integers independently from 1 to 307, and o is an integer from 1 to 21:

Emitter Material

Structure of emitter material

wherein when β is 1, 1-(R1)(R1)(R1)(R1)(R1)(R1) to 1-(R292)(R307)(R307)(R307)(R307)(R307), having the structure

wherein when β is 2, 2-(R1)(R1)(R1)(R1)(R1)(R1) to 2-(R292)(R307)(R307)(R307)(R307)(R307), having the structure

wherein when β is 3, 3-(R1)(R1)(R1)(R1)(R1)(R1) to 3-(R292)(R307)(R307)(R307)(R307)(R307), having the structure

wherein when β is 4, 4-(R1)(R1)(R1)(R1)(R1)(R1) to 4-(R292)(R307)(R307)(R307)(R307)(R307), having the structure

wherein when β is 5, 5-(R1)(R1)(R1)(R1)(R1)(R1) to 5-(R292)(R307)(R307)(R307)(R307)(R307), having the structure

wherein when β is 6, 6-(R1)(R1)(R1)(R1)(R1)(R1) to 6-(R292)(R307)(R307)(R307)(R307)(R307), having the structure

wherein when β is 7, 7-(R1)(R1)(R1)(R1)(R1)(R1) to 7-(R292)(R307)(R307)(R307)(R307)(R307), having the structure

wherein when β is 8, 8-(R1)(R1)(R1)(R1)(R1)(R1) to 8-(R292)(R307)(R307)(R307)(R307)(R307), having the structure

wherein when β is 9, 9-(R1)(R1)(R1)(R1)(R1)(R1) to 9-(R292)(R307)(R307)(R307)(R307)(R307), having the structure

wherein when β is 10, 10-(R1)(R1)(R1)(R1)(R1)(R1) to 10-(R292)(R307)(R307)(R307)(R307)(R307), having the structure

wherein when β is 11, 11-(R1)(R1)(R1)(R1)(R1)(R1) to 11-(R292)(R307)(R307)(R307)(R307)(R307), having the structure

wherein when β is 12, 12-(R1)(R1)(R1)(R1)(R1)(R1) to 12-(R292)(R307)(R307)(R307)(R307)(R307), having the structure

wherein when β is 13, 13-(R1)(R1)(R1)(R1)(R1)(R1) to 13-(R292)(R307)(R307)(R307)(R307)(R307), having the structure

wherein when β is 14, 14-(R1)(R1)(R1)(R1)(R1)(R1) to 14-(R292)(R307)(R307)(R307)(R307)(R307), having the structure

wherein when β is 15, 15-(R1)(R1)(R1)(R1)(R1)(R1) to 15-(R292)(R307)(R307)(R307)(R307)(R307), having the structure

wherein when β′ is 16, 16-(R1)(R1)(R1)(R1)(R1)(R1)(X1) to 16-(R292)(R307)(R307)(R307)(R307)(R307)(X21), having the structure

wherein when β′ is 17, 17-(R1)(R1)(R1)(R1)(R1)(R1)(X1) to 17-(R292)(R307)(R307)(R307)(R307)(R307)(X21), having the structure

wherein when β′ is 18, 18-(R1)(R1)(R1)(R1)(R1)(R1)(X1) to 18-(R292)(R307)(R307)(R307)(R307)(R307)(X21), having the structure

wherein when β′ is 16, 19-(R1)(R1)(R1)(R1)(R1)(R1)(X1) to 19-(R292)(R307)(R307)(R307)(R307)(R307)(X21), having the structure

wherein when β′ is 20, 20-(R1)(R1)(R1)(R1)(R1)(R1)(X1) to 20-(R292)(R307)(R307)(R307)(R307)(R307)(X21), having the structure

wherein when β′ is 21, 21-(R1)(R1)(R1)(R1)(R1)(R1)(X1) to 21-(R292)(R307)(R307)(R307)(R307)(R307)(X21), having the structure

wherein when β′ is 22, 22-(R1)(R1)(R1)(R1)(R1)(R1)(X1) to 22-(R292)(R307)(R307)(R307)(R307)(R307)(X21), having the structure

wherein when β′ is 23, 23-(R1)(R1)(R1)(R1)(R1)(R1)(X1) to 23-(R292)(R307)(R307)(R307)(R307)(R307)(X21), having the structure

wherein when β′ is 24, 24-(R1)(R1)(R1)(R1)(R1)(R1)(X1) to 24-(R292)(R307)(R307)(R307)(R307)(R307)(X21), having the structure

wherein when β′ is 25, 25-(R1)(R1)(R1)(R1)(R1)(R1)(X1) to 25-(R292)(R307)(R307)(R307)(R307)(R307)(X21), having the structure

wherein when β′ is 26, 26-(R1)(R1)(R1)(R1)(R1)(R1)(X1) to 26-(R292)(R307)(R307)(R307)(R307)(R307)(X21), having the structure

wherein when β′ is 27, 27-(R1)(R1)(R1)(R1)(R1)(R1)(X1) to 27-(R292)(R307)(R307)(R307)(R307)(R307)(X21), having the structure

wherein R1 to R307 have the following structures:

wherein X1 to X21 have the following structures:

18. The OLED of claim 13 , wherein the emitter material is selected from the group consisting of:

19. A consumer product comprising an organic light-emitting device (OLED) having an emission spectrum, the OLED comprising:

an anode;

a cathode; and

an organic emissive layer, disposed between the anode and the cathode, comprising:

a first host material having a highest occupied molecular orbital (HOMO) energy and a lowest unoccupied molecular orbital (LUMO) energy; and

an emitter material having a HOMO energy and a LUMO energy;

wherein,

all materials in the organic emissive layer are mixed together;

the emitter material is a phosphorescent metal complex;

High HOMO energy is the highest HOMO energy among all materials in the organic emissive layer;

Low LUMO energy is the lowest LUMO energy among all materials in the organic emissive layer;

a≤E T −ΔE≤b, wherein E T is triplet energy T 1 of the emitter material, which is the lowest T 1 energy among all materials in the organic emissive layer, ΔE is the energy gap between the High HOMO energy and the Low LUMO energy, a is 0.00 up to 0.15 eV, and b is 0.05 up to 0.45 eV; and

wherein root mean squared function (RMSD) value for the emission spectrum of the OLED and an emission spectrum of a reference OLED, whose organic emissive layer consists of the emitter material and an inert host, is not greater than 0.05,

wherein RMSD value is a single value that represents the average difference between the emission spectrum of the OLED and the emission spectrum of the reference OLED at all wavelengths obtained by the following equation:

R

⁢

M

⁢

S

⁢

D

=

1

n

⁢

∑

1

n

(

I

1

(

λ

)

-

I

2

(

λ

)

)

2

,

wherein n is the number of points on the two emission spectrums being compared, and I 1 and I 2 are the normalized intensity spectrums as a function of wavelength, λ.

20. The consumer product of claim 19 , wherein the consumer product is selected from the group consisting of a flat panel display, a computer monitor, a medical monitor, a television, a billboard, a light for interior or exterior illumination and/or signaling, a heads-up display, a fully or partially transparent display, a flexible display, a laser printer, a telephone, a cell phone, tablet, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a micro-display that is less than 2 inches diagonal, a 3-D display, a virtual reality or augmented reality display, a vehicle, a video walls comprising multiple displays tiled together, a theater or stadium screen, and a sign.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 24, 2021
From: THOMPSON, NICHOLAS J.; LIN, CHUN; CHEN, HSIAO-FAN
To: UNIVERSAL DISPLAY CORPORATION
Reel/Frame 056331/0158 →
Continuity (5)
Continuation In Part 17090265 · Nov 5, 2020
Continuation In Part 16841182 · Apr 6, 2020
Continuation In Part 16683507 · Nov 14, 2019
Provisional Application 62772403 · Nov 28, 2018
Related Publication 20210305520A1 · Sep 30, 2021