IP Library Granted Patent US 11,999,886
Granted Patent B2
US 11,999,886 · App. 17/022,149 · Granted Jun 4, 2024

Organic electroluminescent materials and devices

Inventors: Walter Yeager (Yardley, PA); Zhiqiang Ji (Chalfont, PA); Pierre-Luc T. Boudreault (Pennington, NJ)
Assignee: UNIVERSAL DISPLAY CORPORATION
C09K11/06C07F15/0033C09K11/02H10K85/342C09K2211/1007C09K2211/1011C09K2211/1029C09K2211/1037C09K2211/185H10K50/11H10K85/654H10K85/6572H10K2101/10H10K2102/351
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Quick Facts
Patent No.
US 11,999,886
App. No.
17/022,149
Granted
Jun 4, 2024
Kind
B2
Abstract

Provided are compounds including a ligand L A of that are useful as emitters in OLEDs, where at least one of R A and R B is

Claims (3182)

1. A compound comprising a ligand L A of Formula I

wherein:

K 1 is N and K 2 , K 3 , and K 4 are each C;

ring A is a 5-membered or 6-membered carbocyclic or heterocyclic ring;

ring B is a 5-membered or 6-membered carbocyclic or heterocyclic ring;

R A and R B each independently represents zero, mono, or up to the maximum number of allowed substitutions to its associated ring; and

R A and R B is independently a hydrogen or a substituent selected from the group consisting of Formula II, Formula III, Formula IV, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, with at least one of R A and R B comprising Formula II, Formula III, or Formula IV, wherein

wherein:

ring C is a 5-membered or 6-membered carbocyclic or heterocyclic ring;

X in Formula II is N;

Y for each occurrence is independently O, S, Se, or NR;

each of G 1 -G 8 is independently C or N;

R II , R III and R IV each independently represent zero, mono, or up to a maximum allowed substitution to its associated ring;

each of R, R II , R III , and R IV is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;

two substituents can be joined or fused together to form a ring, wherein the ligand L A is coordinated to a metal M through the two indicated dashed lines;

M is selected from the group consisting of Os, Ir, Pd, Pt, Cu, Ag, and Au;

the ligand L A can be linked with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand; and

wherein at least one of the following is true:

i) at least one R II is a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;

ii) at least one R III is partially or fully halogenated and/or a sulfanyl;

iii) two R B join together to form a fused ring; or

iv) Formula II, Formula III, or Formula IV bond to ring B when ring B is a 5-membered or 6-membered carbocyclic ring.

2. The compound of claim 1 , wherein each of R, R II , R III , and R IV is independently a hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof and each of R A and R B is independently a hydrogen or a substituent selected from the group consisting of Formula II, Formula III, Formula IV, deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof with at least one of R A and R B comprising Formula II, Formula III, or Formula IV.

3. The compound of claim 1 , wherein at least one R A comprises a structure of Formula IIA

4. The compound of claim 3 , wherein ring A is a 6-membered aromatic ring, ring B is a 6-membered aromatic ring, or ring C is a 5- or 6-membered aromatic ring.

5. The compound of claim 3 , wherein at least one of the following conditions is true:

two R A substituents are joined to form a 5- or 6-membered fused ring,

two R B substituents are joined together to form a fused 6-membered aromatic ring,

two R II substituents are joined to form a 5- or 6-membered ring, and

two R III substituents are joined to form a 5- or 6-membered ring.

6. The compound of claim 3 , wherein the ligand L A is selected from the group consisting of:

wherein: each X 1 to X 6 is independently selected from the group consisting of C and N;

each Y A1 and Y A2 is independently 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 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, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

7. The compound of claim 3 , wherein the ligand L A is selected from the group consisting of

8. A compound comprising a ligand L A of Formula I

wherein:

K 1 is N and K 2 , K 3 , and K 4 are each C;

ring A is a 5-membered or 6-membered carbocyclic or heterocyclic ring;

ring B is a 6-membered carbocyclic ring;

R A and R B each independently represents zero, mono, or up to the maximum number of allowed substitutions to its associated ring;

wherein the ligand L A has a structure of Formula IB

wherein:

R A and R B is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, with at least one R B comprising a structure of Formula IIA, Formula IIB, Formula IVA, Formula IVB, or Formula V listed below:

wherein:

K 5 -K 8 are each independently C or N;

X 10 -X 13 are each independently C or N;

if R B is Formula IVB, then G 8 is C;

X in Formula IIA is N;

Y for each occurrence is independently O, S, Se, or NR;

ring C and ring D are each independently a 5-membered or 6-membered carbocyclic or heterocyclic ring;

each of R II , R IIa , R IV , and R V is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;

two substituents can be joined or fused together to form a ring, wherein the ligand L A is coordinated to a metal M through the two indicated dashed lines;

M is selected from the group consisting of Os, Ir, Pd, Pt, Cu, Ag, and Au; and

the ligand L A can be linked with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand.

9. The compound of claim 8 , wherein one of G 1 -G 8 is N.

10. The compound of claim 8 , wherein each G 1 -G 8 is C.

11. The compound of claim 8 , wherein the ligand L A is selected from the group consisting of:

wherein Q for each occurrence is independently O, S, or NR; and R is independently H, alkyl, fluoroalkyl, aryl, or heteroaryl.

12. The compound of claim 8 , wherein the ligand L A is selected from the group consisting of:

13. The compound of claim 3 , wherein the compound has a formula of M(L A ) x (L B ) y (L C ) z wherein L B and L C are each a bidentate ligand; and wherein x is 1, 2, or 3; y is 0, 1, or 2; z is 0, 1, or 2; and x+y+z is the oxidation state of the metal M.

14. The compound of claim 13 , wherein L B and L C are each independently selected from the group consisting of:

wherein:

Y 1 to Y 13 are each independently selected from the group consisting of C and N;

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

R a , R b , R e , and R d each independently represents zero, mono, or up to the maximum number of allowed substitution to its associated ring;

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

two adjacent substituents of R a , R b , R e , and R d can be fused or joined to form a ring or form a multidentate ligand.

15. The compound of claim 1 , wherein the compound is selected from the group consisting of

16. An organic light emitting device (OLED) comprising:

an anode;

a cathode; and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a compound comprising a ligand L A of Formula I

wherein:

K 1 is N and K 2 , K 3 , and K 4 are each C;

ring A is a 5-membered or 6-membered carbocyclic or heterocyclic ring;

ring B is a 5-membered or 6-membered carbocyclic or heterocyclic ring;

R A and R B each independently represents zero, mono, or up to the maximum number of allowed substitutions to its associated ring; and

R A and R B is independently a hydrogen or a substituent selected from the group consisting of Formula II, Formula III, Formula IV, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, with at least one of R A and R B comprising Formula II, Formula III, or Formula IV, wherein

wherein:

ring C is a 5-membered or 6-membered carbocyclic or heterocyclic ring;

X in Formula II is N;

Y for each occurrence is independently O, S, Se, or NR;

each of G 1 -G 8 is independently C or N;

R II , R III , and R IV each independently represent zero, mono, or up to a maximum allowed substitution to its associated ring;

each of R, R II , R III , and R IV is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;

two substituents can be joined or fused together to form a ring, wherein the ligand L A is coordinated to a metal M through the two indicated dashed lines;

M is selected from the group consisting of Os, Ir, Pd, Pt, Cu, Ag, and Au;

the ligand L A can be linked with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand; and

wherein at least one of the following is true:

i) at least one R II is a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;

ii) at least one R II is partially or fully halogenated and/or a sulfanyl;

iii) two R B join together to form a fused ring; or

iv) Formula II, Formula III, or Formula IV bond to ring B when ring B is a 5-membered or 6-membered carbocyclic ring.

17. A consumer product comprising an organic light-emitting device (OLED) comprising:

an anode;

a cathode; and

an organic layer disposed between the anode and the cathode, wherein the organic layer comprises the compound of claim 1 .

18. The compound of claim 3 , wherein the ligand L A is selected from the group consisting of L Ai-m , wherein m is an integer from 1 to 36, whose structures are defined as follows:

L Ai-1 based on the structure of

Formula 1

L Ai-2 based on the structure of

Formula 2

L Ai-3 based on the structure of

Formula 3

L Ai-4 based on the structure of

Formula 4

L Ai-5 based on the structure of

Formula 5

L Ai-6 based on the structure of

Formula 6

L Ai-7 based on the structure of

Formula 7

L Ai-8 based on the structure of

Formula 8

L Ai-9 based on the structure of

Formula 9

L Ai-10 based on the structure of

Formula 10

L Ai-11 based on the structure of

Formula 11

L Ai-12 based on the structure of

Formula 12

L Ai-13 based on the structure of

Formula 13

L Ai-14 based on the structure of

Formula 14

L Ai-15 based on the structure of

Formula 15

L Ai-16 based on the structure of

Formula 16

L Ai-17 based on the structure of

Formula 17

L Ai-18 based on the structure of

Formula 18

L Ai-19 based on the structure of

Formula 19

L Ai-20 based on the structure of

Formula 20

L Ai-21 based on the structure of

Formula 21

L Ai-22 based on the structure of

L Ai-23 based on the structure of

L Ai-24 based on the structure of

L Ai-25 based on the structure of

L Ai-26 based on the structure of

L Ai-27 based on the structure of

L Ai-28 based on the structure of

L Ai-29 based on the structure of

L Ai-30 based on the structure of

L Ai-31 based on the structure of

L Ai-32 based on the structure of

L Ai-33 based on the structure of

L Ai-34 based on the structure of

L Ai-35 based on the structure of

L Ai-36 based on the structure of

wherein in Formulas 1, 2, 7, and 8, i is an integer from 37-40, 43-57, 59, 61, 63, 65-67, 69, 71, 73, 75, 77-79, 97-100, 137-140, 143-157, 159, 161, 163, 165-167, 169, 171, 173, 175, 177-190, 197-200, 237-240, 243-257, 259, 261, 263, 265-267, 269, 271, 273, 275, 277-290, 297-300, 337-340, 343-357, 359, 361, 363, 365-367, 369, 371, 373, 375, 377-390, 397-400, 437-440, 443-457, 459, 461, 463, 465-467, 469, 471, 473, 475, 477-490, 497-500, 537-540, 543-557, 559, 561, 563, 565-567, 569, 571, 573, 575, 577-590, 597-600, 637-640, 643-657, 659, 661, 663, 665-667, 669, 671, 673, 675, 677-690, 697-700, 737-740, 743-757, 759, 761, 763, 765-767, 769, 771, 773, 775, 777-790, 797-800, 837-840, 843-857, 859, 861, 863, 865-867, 869, 871, 873, 875, 877-890, 897-900, 937-940, 943-957, 959, 961, 963, 965-967, 969, 971, 973, 975, 977-990, and 997-1000;

wherein in Formulas 3, 4-6, and 9-36, i is an integer from 1 to 1000;

wherein for each L Ai and L Ai-m the substituents R′ and R″ are defined as follows:

L Ai

R’

R”

Ligand

R’

R”

Ligand

R’

R”

Ligand

R’

R”

Ligand

R’

R”

L A1

R a1

R b1

L A201

R a1

R b2

L A401

R a1

R b3

L A601

R a1

R b4

L A801

R a1

R b5

L A2

R a2

R b1

L A202

R a2

R b2

L A402

R a2

R b3

L A602

R a2

R b4

L A802

R a2

R b5

L A3

R a3

R b1

L A203

R a3

R b2

L A403

R a3

R b3

L A603

R a3

R b4

L A803

R a3

R b5

L A4

R a4

R b1

L A204

R a4

R b2

L A404

R a4

R b3

L A604

R a4

R b4

L A804

R a4

R b5

L A5

R a5

R b1

L A205

R a5

R b2

L A405

R a5

R b3

L A605

R a5

R b4

L A805

R a5

R b5

L A6

R a6

R b1

L A206

R a6

R b2

L A406

R a6

R b3

L A606

R a6

R b4

L A806

R a6

R b5

L A7

R a7

R b1

L A207

R a7

R b2

L A407

R a7

R b3

L A607

R a7

R b4

L A807

R a7

R b5

L A8

R a8

R b1

L A208

R a8

R b2

L A408

R a8

R b3

L A608

R a8

R b4

L A808

R a8

R b5

L A9

R a9

R b1

L A209

R a9

R b2

L A409

R a9

R b3

L A609

R a9

R b4

L A809

R a9

R b5

L A10

R a10

R b1

L A210

R a10

R b2

L A410

R a10

R b3

L A610

R a10

R b4

L A810

R a10

R b5

L A11

R a11

R b1

L A211

R a11

R b2

L A411

R a11

R b3

L A611

R a11

R b4

L A811

R a11

R b5

L A12

R a12

R b1

L A212

R a12

R b2

L A412

R a12

R b3

L A612

R a12

R b4

L A812

R a12

R b5

L A13

R a13

R b1

L A213

R a13

R b2

L A413

R a13

R b3

L A613

R a13

R b4

L A813

R a13

R b5

L A14

R a14

R b1

L A214

R a14

R b2

L A414

R a14

R b3

L A614

R a14

R b4

L A814

R a14

R b5

L A15

R a15

R b1

L A215

R a15

R b2

L A415

R a15

R b3

L A615

R a15

R b4

L A815

R a15

R b5

L A16

R a16

R b1

L A216

R a16

R b2

L A416

R a16

R b3

L A616

R a16

R b4

L A816

R a16

R b5

L A17

R a17

R b1

L A217

R a17

R b2

L A417

R a17

R b3

L A617

R a17

R b4

L A817

R a17

R b5

L A18

R a18

R b1

L A218

R a18

R b2

L A418

R a18

R b3

L A618

R a18

R b4

L A818

R a18

R b5

L A19

R a19

R b1

L A219

R a19

R b2

L A419

R a19

R b3

L A619

R a19

R b4

L A819

R a19

R b5

L A20

R a20

R b1

L A220

R a20

R b2

L A420

R a20

R b3

L A620

R a20

R b4

L A820

R a20

R b5

L A21

R a21

R b1

L A221

R a21

R b2

L A421

R a21

R b3

L A621

R a21

R b4

L A821

R a21

R b5

L A22

R a22

R b1

L A222

R a22

R b2

L A422

R a22

R b3

L A622

R a22

R b4

L A822

R a22

R b5

L A23

R a23

R b1

L A223

R a23

R b2

L A423

R a23

R b3

L A623

R a23

R b4

L A823

R a23

R b5

L A24

R a24

R b1

L A224

R a24

R b2

L A424

R a24

R b3

L A624

R a24

R b4

L A824

R a24

R b5

L A25

R a25

R b1

L A225

R a25

R b2

L A425

R a25

R b3

L A625

R a25

R b4

L A825

R a25

R b5

L A26

R a26

R b1

L A226

R a26

R b2

L A426

R a26

R b3

L A626

R a26

R b4

L A826

R a26

R b5

L A27

R a27

R b1

L A227

R a27

R b2

L A427

R a27

R b3

L A627

R a27

R b4

L A827

R a27

R b5

L A28

R a28

R b1

L A228

R a28

R b2

L A428

R a28

R b3

L A628

R a28

R b4

L A828

R a28

R b5

L A29

R a29

R b1

L A229

R a29

R b2

L A429

R a29

R b3

L A629

R a29

R b4

L A829

R a29

R b5

L A30

R a30

R b1

L A230

R a30

R b2

L A430

R a30

R b3

L A630

R a30

R b4

L A830

R a30

R b5

L A31

R a31

R b1

L A231

R a31

R b2

L A431

R a31

R b3

L A631

R a31

R b4

L A831

R a31

R b5

L A32

R a32

R b1

L A232

R a32

R b2

L A432

R a32

R b3

L A632

R a32

R b4

L A832

R a32

R b5

L A33

R a33

R b1

L A233

R a33

R b2

L A433

R a33

R b3

L A633

R a33

R b4

L A833

R a33

R b5

L A34

R a34

R b1

L A234

R a34

R b2

L A434

R a34

R b3

L A634

R a34

R b4

L A834

R a34

R b5

L A35

R a35

R b1

L A235

R a35

R b2

L A435

R a35

R b3

L A635

R a35

R b4

L A835

R a35

R b5

L A36

R a36

R b1

L A236

R a36

R b2

L A436

R a36

R b3

L A636

R a36

R b4

L A836

R a36

R b5

L A37

R a37

R b1

L A237

R a37

R b2

L A437

R a37

R b3

L A637

R a37

R b4

L A837

R a37

R b5

L A38

R a38

R b1

L A238

R a38

R b2

L A438

R a38

R b3

L A638

R a38

R b4

L A838

R a38

R b5

L A39

R a39

R b1

L A239

R a39

R b2

L A439

R a39

R b3

L A639

R a39

R b4

L A839

R a39

R b5

L A40

R a40

R b1

L A240

R a40

R b2

L A440

R a40

R b3

L A640

R a40

R b4

L A840

R a40

R b5

L A41

R a41

R b1

L A241

R a41

R b2

L A441

R a41

R b3

L A641

R a41

R b4

L A841

R a41

R b5

L A42

R a42

R b1

L A242

R a42

R b2

L A442

R a42

R b3

L A642

R a42

R b4

L A842

R a42

R b5

L A43

R a43

R b1

L A243

R a43

R b2

L A443

R a43

R b3

L A643

R a43

R b4

L A843

R a43

R b5

L A44

R a44

R b1

L A244

R a44

R b2

L A444

R a44

R b3

L A644

R a44

R b4

L A844

R a44

R b5

L A45

R a45

R b1

L A245

R a45

R b2

L A445

R a45

R b3

L A645

R a45

R b4

L A845

R a45

R b5

L A46

R a46

R b1

L A246

R a46

R b2

L A446

R a46

R b3

L A646

R a46

R b4

L A846

R a46

R b5

L A47

R a47

R b1

L A247

R a47

R b2

L A447

R a47

R b3

L A647

R a47

R b4

L A847

R a47

R b5

L A48

R a48

R b1

L A248

R a48

R b2

L A448

R a48

R b3

L A648

R a48

R b4

L A848

R a48

R b5

L A49

R a49

R b1

L A249

R a49

R b2

L A449

R a49

R b3

L A649

R a49

R b4

L A849

R a49

R b5

L A50

R a50

R b1

L A250

R a50

R b2

L A450

R a50

R b3

L A650

R a50

R b4

L A850

R a50

R b5

L A51

R a51

R b1

L A251

R a51

R b2

L A451

R a51

R b3

L A651

R a51

R b4

L A851

R a51

R b5

L A52

R a52

R b1

L A252

R a52

R b2

L A452

R a52

R b3

L A652

R a52

R b4

L A852

R a52

R b5

L A53

R a53

R b1

L A253

R a53

R b2

L A453

R a53

R b3

L A653

R a53

R b4

L A853

R a53

R b5

L A54

R a54

R b1

L A254

R a54

R b2

L A454

R a54

R b3

L A654

R a54

R b4

L A854

R a54

R b5

L A55

R a55

R b1

L A255

R a55

R b2

L A455

R a55

R b3

L A655

R a55

R b4

L A855

R a55

R b5

L A56

R a56

R b1

L A256

R a56

R b2

L A456

R a56

R b3

L A656

R a56

R b4

L A856

R a56

R b5

L A57

R a57

R b1

L A257

R a57

R b2

L A457

R a57

R b3

L A657

R a57

R b4

L A857

R a57

R b5

L A58

R a58

R b1

L A258

R a58

R b2

L A458

R a58

R b3

L A658

R a58

R b4

L A858

R a58

R b5

L A59

R a59

R b1

L A259

R a59

R b2

L A459

R a59

R b3

L A659

R a59

R b4

L A859

R a59

R b5

L A60

R a60

R b1

L A260

R a60

R b2

L A460

R a60

R b3

L A660

R a60

R b4

L A860

R a60

R b5

L A61

R a61

R b1

L A261

R a61

R b2

L A461

R a61

R b3

L A661

R a61

R b4

L A861

R a61

R b5

L A62

R a62

R b1

L A262

R a62

R b2

L A462

R a62

R b3

L A662

R a62

R b4

L A862

R a62

R b5

L A63

R a63

R b1

L A263

R a63

R b2

L A463

R a63

R b3

L A663

R a63

R b4

L A863

R a63

R b5

L A64

R a64

R b1

L A264

R a64

R b2

L A464

R a64

R b3

L A664

R a64

R b4

L A864

R a64

R b5

L A65

R a65

R b1

L A265

R a65

R b2

L A465

R a65

R b3

L A665

R a65

R b4

L A865

R a65

R b5

L A66

R a66

R b1

L A266

R a66

R b2

L A466

R a66

R b3

L A666

R a66

R b4

L A866

R a66

R b5

L A67

R a67

R b1

L A267

R a67

R b2

L A467

R a67

R b3

L A667

R a67

R b4

L A867

R a67

R b5

L A68

R a68

R b1

L A268

R a68

R b2

L A468

R a68

R b3

L A668

R a68

R b4

L A868

R a68

R b5

L A69

R a69

R b1

L A269

R a69

R b2

L A469

R a69

R b3

L A669

R a69

R b4

L A869

R a69

R b5

L A70

R a70

R b1

L A270

R a70

R b2

L A470

R a70

R b3

L A670

R a70

R b4

L A870

R a70

R b5

L A71

R a71

R b1

L A271

R a71

R b2

L A471

R a71

R b3

L A671

R a71

R b4

L A871

R a71

R b5

L A72

R a72

R b1

L A272

R a72

R b2

L A472

R a72

R b3

L A672

R a72

R b4

L A872

R a72

R b5

L A73

R a73

R b1

L A273

R a73

R b2

L A473

R a73

R b3

L A673

R a73

R b4

L A873

R a73

R b5

L A74

R a74

R b1

L A274

R a74

R b2

L A474

R a74

R b3

L A674

R a74

R b4

L A874

R a74

R b5

L A75

R a75

R b1

L A275

R a75

R b2

L A475

R a75

R b3

L A675

R a75

R b4

L A875

R a75

R b5

L A76

R a76

R b1

L A276

R a76

R b2

L A476

R a76

R b3

L A676

R a76

R b4

L A876

R a76

R b5

L A77

R a77

R b1

L A277

R a77

R b2

L A477

R a77

R b3

L A677

R a77

R b4

L A877

R a77

R b5

L A78

R a78

R b1

L A278

R a78

R b2

L A478

R a78

R b3

L A678

R a78

R b4

L A878

R a78

R b5

L A79

R a79

R b1

L A279

R a79

R b2

L A479

R a79

R b3

L A679

R a79

R b4

L A879

R a79

R b5

L A80

R a80

R b1

L A280

R a80

R b2

L A480

R a80

R b3

L A680

R a80

R b4

L A880

R a80

R b5

L A81

R a81

R b1

L A281

R a81

R b2

L A481

R a81

R b3

L A681

R a81

R b4

L A881

R a81

R b5

L A82

R a82

R b1

L A282

R a82

R b2

L A482

R a82

R b3

L A682

R a82

R b4

L A882

R a82

R b5

L A83

R a83

R b1

L A283

R a83

R b2

L A483

R a83

R b3

L A683

R a83

R b4

L A883

R a83

R b5

L A84

R a84

R b1

L A284

R a84

R b2

L A484

R a84

R b3

L A684

R a84

R b4

L A884

R a84

R b5

L A85

R a85

R b1

L A285

R a85

R b2

L A485

R a85

R b3

L A685

R a85

R b4

L A885

R a85

R b5

L A86

R a86

R b1

L A286

R a86

R b2

L A486

R a86

R b3

L A686

R a86

R b4

L A886

R a86

R b5

L A87

R a87

R b1

L A287

R a87

R b2

L A487

R a87

R b3

L A687

R a87

R b4

L A887

R a87

R b5

L A88

R a88

R b1

L A288

R a88

R b2

L A488

R a88

R b3

L A688

R a88

R b4

L A888

R a88

R b5

L A89

R a89

R b1

L A289

R a89

R b2

L A489

R a89

R b3

L A689

R a89

R b4

L A889

R a89

R b5

L A90

R a90

R b1

L A290

R a90

R b2

L A490

R a90

R b3

L A690

R a90

R b4

L A890

R a90

R b5

L A91

R a91

R b1

L A291

R a91

R b2

L A491

R a91

R b3

L A691

R a91

R b4

L A891

R a91

R b5

L A92

R a92

R b1

L A292

R a92

R b2

L A492

R a92

R b3

L A692

R a92

R b4

L A892

R a92

R b5

L A93

R a93

R b1

L A293

R a93

R b2

L A493

R a93

R b3

L A693

R a93

R b4

L A893

R a93

R b5

L A94

R a94

R b1

L A294

R a94

R b2

L A494

R a94

R b3

L A694

R a94

R b4

L A894

R a94

R b5

L A95

R a95

R b1

L A295

R a95

R b2

L A495

R a95

R b3

L A695

R a95

R b4

L A895

R a95

R b5

L A96

R a96

R b1

L A296

R a96

R b2

L A496

R a96

R b3

L A696

R a96

R b4

L A896

R a96

R b5

L A97

R a97

R b1

L A297

R a97

R b2

L A497

R a97

R b3

L A697

R a97

R b4

L A897

R a97

R b5

L A98

R a98

R b1

L A298

R a98

R b2

L A498

R a98

R b3

L A698

R a98

R b4

L A898

R a98

R b5

L A99

R a99

R b1

L A299

R a99

R b2

L A499

R a99

R b3

L A699

R a99

R b4

L A899

R a99

R b5

L A100

R a100

R b1

L A300

R a100

R b2

L A500

R a100

R b3

L A700

R a100

R b4

L A900

R a100

R b5

L A101

R a1

R b6

L A301

R a1

R b7

L A501

R a1

R b8

L A701

R a1

R b9

L A901

R a1

R b10

L A102

R a2

R b6

L A302

R a2

R b7

L A502

R a2

R b8

L A702

R a2

R b9

L A902

R a2

R b10

L A103

R a3

R b6

L A303

R a3

R b7

L A503

R a3

R b8

L A703

R a3

R b9

L A903

R a3

R b10

L A104

R a4

R b6

L A304

R a4

R b7

L A504

R a4

R b8

L A704

R a4

R b9

L A904

R a4

R b10

L A105

R a5

R b6

L A305

R a5

R b7

L A505

R a5

R b8

L A705

R a5

R b9

L A905

R a5

R b10

L A106

R a6

R b6

L A306

R a6

R b7

L A506

R a6

R b8

L A706

R a6

R b9

L A906

R a6

R b10

L A107

R a7

R b6

L A307

R a7

R b7

L A507

R a7

R b8

L A707

R a7

R b9

L A907

R a7

R b10

L A108

R a8

R b6

L A308

R a8

R b7

L A508

R a8

R b8

L A708

R a8

R b9

L A908

R a8

R b10

L A109

R a9

R b6

L A309

R a9

R b7

L A509

R a9

R b8

L A709

R a9

R b9

L A909

R a9

R b10

L A110

R a10

R b6

L A310

R a10

R b7

L A510

R a10

R b8

L A710

R a10

R b9

L A910

R a10

R b10

L A111

R a11

R b6

L A311

R a11

R b7

L A511

R a11

R b8

L A711

R a11

R b9

L A911

R a11

R b10

L A112

R a12

R b6

L A312

R a12

R b7

L A512

R a12

R b8

L A712

R a12

R b9

L A912

R a12

R b10

L A113

R a13

R b6

L A313

R a13

R b7

L A513

R a13

R b8

L A713

R a13

R b9

L A913

R a13

R b10

L A114

R a14

R b6

L A314

R a14

R b7

L A514

R a14

R b8

L A714

R a14

R b9

L A914

R a14

R b10

L A115

R a15

R b6

L A315

R a15

R b7

L A515

R a15

R b8

L A715

R a15

R b9

L A915

R a15

R b10

L A116

R a16

R b6

L A316

R a16

R b7

L A516

R a16

R b8

L A716

R a16

R b9

L A916

R a16

R b10

L A117

R a17

R b6

L A317

R a17

R b7

L A517

R a17

R b8

L A717

R a17

R b9

L A917

R a17

R b10

L A118

R a18

R b6

L A318

R a18

R b7

L A518

R a18

R b8

L A718

R a18

R b9

L A918

R a18

R b10

L A119

R a19

R b6

L A319

R a19

R b7

L A519

R a19

R b8

L A719

R a19

R b9

L A919

R a19

R b10

L A120

R a20

R b6

L A320

R a20

R b7

L A520

R a20

R b8

L A720

R a20

R b9

L A920

R a20

R b10

L A121

R a21

R b6

L A321

R a21

R b7

L A521

R a21

R b8

L A721

R a21

R b9

L A921

R a21

R b10

L A122

R a22

R b6

L A322

R a22

R b7

L A522

R a22

R b8

L A722

R a22

R b9

L A922

R a22

R b10

L A123

R a23

R b6

L A323

R a23

R b7

L A523

R a23

R b8

L A723

R a23

R b9

L A923

R a23

R b10

L A124

R a24

R b6

L A324

R a24

R b7

L A524

R a24

R b8

L A724

R a24

R b9

L A924

R a24

R b10

L A125

R a25

R b6

L A325

R a25

R b7

L A525

R a25

R b8

L A725

R a25

R b9

L A925

R a25

R b10

L A126

R a26

R b6

L A326

R a26

R b7

L A526

R a26

R b8

L A726

R a26

R b9

L A926

R a26

R b10

L A127

R a27

R b6

L A327

R a27

R b7

L A527

R a27

R b8

L A727

R a27

R b9

L A927

R a27

R b10

L A128

R a28

R b6

L A328

R a28

R b7

L A528

R a28

R b8

L A728

R a28

R b9

L A928

R a28

R b10

L A129

R a29

R b6

L A329

R a29

R b7

L A529

R a29

R b8

L A729

R a29

R b9

L A929

R a29

R b10

L A130

R a30

R b6

L A330

R a30

R b7

L A530

R a30

R b8

L A730

R a30

R b9

L A930

R a30

R b10

L A131

R a31

R b6

L A331

R a31

R b7

L A531

R a31

R b8

L A731

R a31

R b9

L A931

R a31

R b10

L A132

R a32

R b6

L A332

R a32

R b7

L A532

R a32

R b8

L A732

R a32

R b9

L A932

R a32

R b10

L A133

R a33

R b6

L A333

R a33

R b7

L A533

R a33

R b8

L A733

R a33

R b9

L A933

R a33

R b10

L A134

R a34

R b6

L A334

R a34

R b7

L A534

R a34

R b8

L A734

R a34

R b9

L A934

R a34

R b10

L A135

R a35

R b6

L A335

R a35

R b7

L A535

R a35

R b8

L A735

R a35

R b9

L A935

R a35

R b10

L A136

R a36

R b6

L A336

R a36

R b7

L A536

R a36

R b8

L A736

R a36

R b9

L A936

R a36

R b10

L A137

R a37

R b6

L A337

R a37

R b7

L A537

R a37

R b8

L A737

R a37

R b9

L A937

R a37

R b10

L A138

R a38

R b6

L A338

R a38

R b7

L A538

R a38

R b8

L A738

R a38

R b9

L A938

R a38

R b10

L A139

R a39

R b6

L A339

R a39

R b7

L A539

R a39

R b8

L A739

R a39

R b9

L A939

R a39

R b10

L A140

R a40

R b6

L A340

R a40

R b7

L A540

R a40

R b8

L A740

R a40

R b9

L A940

R a40

R b10

L A141

R a41

R b6

L A341

R a41

R b7

L A541

R a41

R b8

L A741

R a41

R b9

L A941

R a41

R b10

L A142

R a42

R b6

L A342

R a42

R b7

L A542

R a42

R b8

L A742

R a42

R b9

L A942

R a42

R b10

L A143

R a43

R b6

L A343

R a43

R b7

L A543

R a43

R b8

L A743

R a43

R b9

L A943

R a43

R b10

L A144

R a44

R b6

L A344

R a44

R b7

L A544

R a44

R b8

L A744

R a44

R b9

L A944

R a44

R b10

L A145

R a45

R b6

L A345

R a45

R b7

L A545

R a45

R b8

L A745

R a45

R b9

L A945

R a45

R b10

L A146

R a46

R b6

L A346

R a46

R b7

L A546

R a46

R b8

L A746

R a46

R b9

L A946

R a46

R b10

L A147

R a47

R b6

L A347

R a47

R b7

L A547

R a47

R b8

L A747

R a47

R b9

L A947

R a47

R b10

L A148

R a48

R b6

L A348

R a48

R b7

L A548

R a48

R b8

L A748

R a48

R b9

L A948

R a48

R b10

L A149

R a49

R b6

L A349

R a49

R b7

L A549

R a49

R b8

L A749

R a49

R b9

L A949

R a49

R b10

L A150

R a50

R b6

L A350

R a50

R b7

L A550

R a50

R b8

L A750

R a50

R b9

L A950

R a50

R b10

L A151

R a51

R b6

L A351

R a51

R b7

L A551

R a51

R b8

L A751

R a51

R b9

L A951

R a51

R b10

L A152

R a52

R b6

L A352

R a52

R b7

L A552

R a52

R b8

L A752

R a52

R b9

L A952

R a52

R b10

L A153

R a53

R b6

L A353

R a53

R b7

L A553

R a53

R b8

L A753

R a53

R b9

L A953

R a53

R b10

L A154

R a54

R b6

L A354

R a54

R b7

L A554

R a54

R b8

L A754

R a54

R b9

L A954

R a54

R b10

L A155

R a55

R b6

L A355

R a55

R b7

L A555

R a55

R b8

L A755

R a55

R b9

L A955

R a55

R b10

L A156

R a56

R b6

L A356

R a56

R b7

L A556

R a56

R b8

L A756

R a56

R b9

L A956

R a56

R b10

L A157

R a57

R b6

L A357

R a57

R b7

L A557

R a57

R b8

L A757

R a57

R b9

L A957

R a57

R b10

L A158

R a58

R b6

L A358

R a58

R b7

L A558

R a58

R b8

L A758

R a58

R b9

L A958

R a58

R b10

L A159

R a59

R b6

L A359

R a59

R b7

L A559

R a59

R b8

L A759

R a59

R b9

L A959

R a59

R b10

L A160

R a60

R b6

L A360

R a60

R b7

L A560

R a60

R b8

L A760

R a60

R b9

L A960

R a60

R b10

L A161

R a61

R b6

L A361

R a61

R b7

L A561

R a61

R b8

L A761

R a61

R b9

L A961

R a61

R b10

L A162

R a62

R b6

L A362

R a62

R b7

L A562

R a62

R b8

L A762

R a62

R b9

L A962

R a62

R b10

L A163

R a63

R b6

L A363

R a63

R b7

L A563

R a63

R b8

L A763

R a63

R b9

L A963

R a63

R b10

L A164

R a64

R b6

L A364

R a64

R b7

L A564

R a64

R b8

L A764

R a64

R b9

L A964

R a64

R b10

L A165

R a65

R b6

L A365

R a65

R b7

L A565

R a65

R b8

L A765

R a65

R b9

L A965

R a65

R b10

L A166

R a66

R b6

L A366

R a66

R b7

L A566

R a66

R b8

L A766

R a66

R b9

L A966

R a66

R b10

L A167

R a67

R b6

L A367

R a67

R b7

L A567

R a67

R b8

L A767

R a67

R b9

L A967

R a67

R b10

L A168

R a68

R b6

L A368

R a68

R b7

L A568

R a68

R b8

L A768

R a68

R b9

L A968

R a68

R b10

L A169

R a69

R b6

L A369

R a69

R b7

L A569

R a69

R b8

L A769

R a69

R b9

L A969

R a69

R b10

L A170

R a70

R b6

L A370

R a70

R b7

L A570

R a70

R b8

L A770

R a70

R b9

L A970

R a70

R b10

L A171

R a71

R b6

L A371

R a71

R b7

L A571

R a71

R b8

L A771

R a71

R b9

L A971

R a71

R b10

L A172

R a72

R b6

L A372

R a72

R b7

L A572

R a72

R b8

L A772

R a72

R b9

L A972

R a72

R b10

L A173

R a73

R b6

L A373

R a73

R b7

L A573

R a73

R b8

L A773

R a73

R b9

L A973

R a73

R b10

L A174

R a74

R b6

L A374

R a74

R b7

L A574

R a74

R b8

L A774

R a74

R b9

L A974

R a74

R b10

L A175

R a75

R b6

L A375

R a75

R b7

L A575

R a75

R b8

L A775

R a75

R b9

L A975

R a75

R b10

L A176

R a76

R b6

L A376

R a76

R b7

L A576

R a76

R b8

L A776

R a76

R b9

L A976

R a76

R b10

L A177

R a77

R b6

L A377

R a77

R b7

L A577

R a77

R b8

L A777

R a77

R b9

L A977

R a77

R b10

L A178

R a78

R b6

L A378

R a78

R b7

L A578

R a78

R b8

L A778

R a78

R b9

L A978

R a78

R b10

L A179

R a79

R b6

L A379

R a79

R b7

L A579

R a79

R b8

L A779

R a79

R b9

L A979

R a79

R b10

L A180

R a80

R b6

L A380

R a80

R b7

L A580

R a80

R b8

L A780

R a80

R b9

L A980

R a80

R b10

L A181

R a81

R b6

L A381

R a81

R b7

L A581

R a81

R b8

L A781

R a81

R b9

L A981

R a81

R b10

L A182

R a82

R b6

L A382

R a82

R b7

L A582

R a82

R b8

L A782

R a82

R b9

L A982

R a82

R b10

L A183

R a83

R b6

L A383

R a83

R b7

L A583

R a83

R b8

L A783

R a83

R b9

L A983

R a83

R b10

L A184

R a84

R b6

L A384

R a84

R b7

L A584

R a84

R b8

L A784

R a84

R b9

L A984

R a84

R b10

L A185

R a85

R b6

L A385

R a85

R b7

L A585

R a85

R b8

L A785

R a85

R b9

L A985

R a85

R b10

L A186

R a86

R b6

L A386

R a86

R b7

L A586

R a86

R b8

L A786

R a86

R b9

L A986

R a86

R b10

L A187

R a87

R b6

L A387

R a87

R b7

L A587

R a87

R b8

L A787

R a87

R b9

L A987

R a87

R b10

L A188

R a88

R b6

L A388

R a88

R b7

L A588

R a88

R b8

L A788

R a88

R b9

L A988

R a88

R b10

L A189

R a89

R b6

L A389

R a89

R b7

L A589

R a89

R b8

L A789

R a89

R b9

L A989

R a89

R b10

L A190

R a90

R b6

L A390

R a90

R b7

L A590

R a90

R b8

L A790

R a90

R b9

L A990

R a90

R b10

L A191

R a91

R b6

L A391

R a91

R b7

L A591

R a91

R b8

L A791

R a91

R b9

L A991

R a91

R b10

L A192

R a92

R b6

L A392

R a92

R b7

L A592

R a92

R b8

L A792

R a92

R b9

L A992

R a92

R b10

L A193

R a93

R b6

L A393

R a93

R b7

L A593

R a93

R b8

L A793

R a93

R b9

L A993

R a93

R b10

L A194

R a94

R b6

L A394

R a94

R b7

L A594

R a94

R b8

L A794

R a94

R b9

L A994

R a94

R b10

L A195

R a95

R b6

L A395

R a95

R b7

L A595

R a95

R b8

L A795

R a95

R b9

L A995

R a95

R b10

L A196

R a96

R b6

L A396

R a96

R b7

L A596

R a96

R b8

L A796

R a96

R b9

L A996

R a96

R b10

L A197

R a97

R b6

L A397

R a97

R b7

L A597

R a97

R b8

L A797

R a97

R b9

L A997

R a97

R b10

L A198

R a98

R b6

L A398

R a98

R b7

L A598

R a98

R b8

L A798

R a98

R b9

L A998

R a98

R b10

L A199

R a99

R b6

L A399

R a99

R b7

L A599

R a99

R b8

L A799

R a99

R b9

L A999

R a99

R b10

L A200

R a100

R b6

L A400

R a100

R b7

L A600

R a100

R b8

L A800

R a100

R b9

L A1000

R a100

R b10

wherein R b1 to R b10 have the following structures:

wherein R a1 to R a100 have the following structures:

19. An organic light emitting device (OLED) comprising:

an anode;

a cathode; and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises the compound of claim 8 .

20. A consumer product comprising an organic light-emitting device (OLED) comprising:

an anode;

a cathode; and

an organic layer disposed between the anode and the cathode, wherein the organic layer comprises the compound of claim 8 .

Assignments (1)
NUNC PRO TUNC ASSIGNMENT Recorded Sep 16, 2020
From: YEAGER, WALTER; JI, ZHIQIANG; BOUDREAULT, PIERRE-LUC T.
To: UNIVERSAL DISPLAY CORPORATION
Reel/Frame 053782/0494 →
Continuity (3)
Provisional Application 63010815 · Apr 16, 2020
Provisional Application 62906305 · Sep 26, 2019
Related Publication 20210095196A1 · Apr 1, 2021
Cited By (1)
US 12,262,630