# US 11,999,886 B2 · Organic electroluminescent materials and devices

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- Number: US 11,999,886 B2
- Document ID: US11999886B2
- Status: Granted
- Kind: B2
- Application number: 17/022,149
- Filed: 2020-09-16
- Published: 2021-04-01
- Granted: 2024-06-04
- Earliest claimed: 2019-09-26
- Assignees: Universal Display Corporation
- Applicants: Universal Display Corporation
- Inventors: Walter Yeager; Zhiqiang Ji; Pierre-Luc T. Boudreault
- Web page: https://patentgrep.com/patent/US11999886B2

## CPC

- C09K 11/06: containing organic luminescent materials
- C07F 15/0033: {Iridium compounds}
- C09K 11/02: Use of particular materials as binders, particle coatings or suspension media therefor
- H10K 85/342: {comprising iridium}
- C09K 2211/1007: Non-condensed systems
- C09K 2211/1011: Condensed systems
- C09K 2211/1029: containing one nitrogen atom as the heteroatom
- C09K 2211/1037: with sulfur
- C09K 2211/185: of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 50/121: {for assisting energy transfer, e.g. sensitization}
- H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)}
- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- H10K 2101/10: Triplet emission
- H10K 2102/351: {Thickness}
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES

## Abstract

Provided are compounds including a ligand LA of that are useful as emitters in OLEDs, where at least one of RA and RB is

## Claims

### Claim 1

A compound comprising a ligand LA of Formula I
wherein:
K1 is N and K2, K3, and K4 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;
RA and RB each independently represents zero, mono, or up to the maximum number of allowed substitutions to its associated ring; and
RA and RB 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 RA and RB 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 G1-G8 is independently C or N;
RII, RIII and RIV each independently represent zero, mono, or up to a maximum allowed substitution to its associated ring;
each of R, RII, RIII, and RIV 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 LA 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 LA 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 RII 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 RIII is partially or fully halogenated and/or a sulfanyl;
iii) two RB 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.

### Claim 2 (depends on 1)

The compound of claim 1, wherein each of R, RII, RIII, and RIV 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 RA and RB 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 RA and RB comprising Formula II, Formula III, or Formula IV.

### Claim 3 (depends on 1)

The compound of claim 1, wherein at least one RA comprises a structure of Formula IIA

### Claim 4 (depends on 3)

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.

### Claim 5 (depends on 3)

The compound of claim 3, wherein at least one of the following conditions is true:
two RA substituents are joined to form a 5- or 6-membered fused ring,
two RB substituents are joined together to form a fused 6-membered aromatic ring,
two RII substituents are joined to form a 5- or 6-membered ring, and
two RIII substituents are joined to form a 5- or 6-membered ring.

### Claim 6 (depends on 3)

The compound of claim 3, wherein the ligand LA is selected from the group consisting of:
wherein: each X1 to X6 is independently selected from the group consisting of C and N;
each YA1 and YA2 is independently selected from the group consisting of BRe, NRe, PRe, O, S, Se, C═O, S═O, SO2, CReRf, SiReRf, and GeReRf; Re and Rf can be fused or joined to form a ring;
each Re and Rf 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.

### Claim 7 (depends on 3)

The compound of claim 3, wherein the ligand LA is selected from the group consisting of

### Claim 8

A compound comprising a ligand LA of Formula I
wherein:
K1 is N and K2, K3, and K4 are each C;
ring A is a 5-membered or 6-membered carbocyclic or heterocyclic ring;
ring B is a 6-membered carbocyclic ring;
RA and RB each independently represents zero, mono, or up to the maximum number of allowed substitutions to its associated ring;
wherein the ligand LA has a structure of Formula IB
wherein:
RA and RB 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 RB comprising a structure of Formula IIA, Formula IIB, Formula IVA, Formula IVB, or Formula V listed below:
wherein:
K5-K8 are each independently C or N;
X10-X13 are each independently C or N;
if RB is Formula IVB, then G8 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 RII, RIIa, RIV, and RV 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 LA 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 LA can be linked with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand.

### Claim 9 (depends on 8)

The compound of claim 8, wherein one of G1-G8 is N.

### Claim 10 (depends on 8)

The compound of claim 8, wherein each G1-G8 is C.

### Claim 11 (depends on 8)

The compound of claim 8, wherein the ligand LA 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.

### Claim 12 (depends on 8)

The compound of claim 8, wherein the ligand LA is selected from the group consisting of:

### Claim 13 (depends on 3)

The compound of claim 3, wherein the compound has a formula of M(LA)x(LB)y(LC)z wherein LB and LC 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.

### Claim 14 (depends on 13)

The compound of claim 13, wherein LB and LC are each independently selected from the group consisting of:
wherein:
Y1 to Y13 are each independently selected from the group consisting of C and N;
Y′ is selected from the group consisting of BRe, NRe, PRe, O, S, Se, C═O, S═O, SO2, CReRf, SiReRf, and GeReRf; wherein Re and Rf can be fused or joined to form a ring;
Ra, Rb, Re, and Rd each independently represents zero, mono, or up to the maximum number of allowed substitution to its associated ring;
each Ra, Rb, Re, Rd, Re and Rf 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 Ra, Rb, Re, and Rd can be fused or joined to form a ring or form a multidentate ligand.

### Claim 15 (depends on 1)

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

### Claim 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 LA of Formula I
wherein:
K1 is N and K2, K3, and K4 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;
RA and RB each independently represents zero, mono, or up to the maximum number of allowed substitutions to its associated ring; and
RA and RB 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 RA and RB 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 G1-G8 is independently C or N;
RII, RIII, and RIV each independently represent zero, mono, or up to a maximum allowed substitution to its associated ring;
each of R, RII, RIII, and RIV 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 LA 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 LA 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 RII 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 RII is partially or fully halogenated and/or a sulfanyl;
iii) two RB 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.

### Claim 17 (depends on 1)

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.

### Claim 18 (depends on 3)

The compound of claim 3, wherein the ligand LA is selected from the group consisting of LAi-m, wherein m is an integer from 1 to 36, whose structures are defined as follows:
LAi-1 based on the structure of
Formula 1
LAi-2 based on the structure of
Formula 2
LAi-3 based on the structure of
Formula 3
LAi-4 based on the structure of
Formula 4
LAi-5 based on the structure of
Formula 5
LAi-6 based on the structure of
Formula 6
LAi-7 based on the structure of
Formula 7
LAi-8 based on the structure of
Formula 8
LAi-9 based on the structure of
Formula 9
LAi-10 based on the structure of
Formula 10
LAi-11 based on the structure of
Formula 11
LAi-12 based on the structure of
Formula 12
LAi-13 based on the structure of
Formula 13
LAi-14 based on the structure of
Formula 14
LAi-15 based on the structure of
Formula 15
LAi-16 based on the structure of
Formula 16
LAi-17 based on the structure of
Formula 17
LAi-18 based on the structure of
Formula 18
LAi-19 based on the structure of
Formula 19
LAi-20 based on the structure of
Formula 20
LAi-21 based on the structure of
Formula 21
LAi-22 based on the structure of
LAi-23 based on the structure of
LAi-24 based on the structure of
LAi-25 based on the structure of
LAi-26 based on the structure of
LAi-27 based on the structure of
LAi-28 based on the structure of
LAi-29 based on the structure of
LAi-30 based on the structure of
LAi-31 based on the structure of
LAi-32 based on the structure of
LAi-33 based on the structure of
LAi-34 based on the structure of
LAi-35 based on the structure of
LAi-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 LAi and LAi-m the substituents R′ and R″ are defined as follows:
LAi
R’
R”
Ligand
R’
R”
Ligand
R’
R”
Ligand
R’
R”
Ligand
R’
R”
LA1
Ra1
Rb1
LA201
Ra1
Rb2
LA401
Ra1
Rb3
LA601
Ra1
Rb4
LA801
Ra1
Rb5
LA2
Ra2
Rb1
LA202
Ra2
Rb2
LA402
Ra2
Rb3
LA602
Ra2
Rb4
LA802
Ra2
Rb5
LA3
Ra3
Rb1
LA203
Ra3
Rb2
LA403
Ra3
Rb3
LA603
Ra3
Rb4
LA803
Ra3
Rb5
LA4
Ra4
Rb1
LA204
Ra4
Rb2
LA404
Ra4
Rb3
LA604
Ra4
Rb4
LA804
Ra4
Rb5
LA5
Ra5
Rb1
LA205
Ra5
Rb2
LA405
Ra5
Rb3
LA605
Ra5
Rb4
LA805
Ra5
Rb5
LA6
Ra6
Rb1
LA206
Ra6
Rb2
LA406
Ra6
Rb3
LA606
Ra6
Rb4
LA806
Ra6
Rb5
LA7
Ra7
Rb1
LA207
Ra7
Rb2
LA407
Ra7
Rb3
LA607
Ra7
Rb4
LA807
Ra7
Rb5
LA8
Ra8
Rb1
LA208
Ra8
Rb2
LA408
Ra8
Rb3
LA608
Ra8
Rb4
LA808
Ra8
Rb5
LA9
Ra9
Rb1
LA209
Ra9
Rb2
LA409
Ra9
Rb3
LA609
Ra9
Rb4
LA809
Ra9
Rb5
LA10
Ra10
Rb1
LA210
Ra10
Rb2
LA410
Ra10
Rb3
LA610
Ra10
Rb4
LA810
Ra10
Rb5
LA11
Ra11
Rb1
LA211
Ra11
Rb2
LA411
Ra11
Rb3
LA611
Ra11
Rb4
LA811
Ra11
Rb5
LA12
Ra12
Rb1
LA212
Ra12
Rb2
LA412
Ra12
Rb3
LA612
Ra12
Rb4
LA812
Ra12
Rb5
LA13
Ra13
Rb1
LA213
Ra13
Rb2
LA413
Ra13
Rb3
LA613
Ra13
Rb4
LA813
Ra13
Rb5
LA14
Ra14
Rb1
LA214
Ra14
Rb2
LA414
Ra14
Rb3
LA614
Ra14
Rb4
LA814
Ra14
Rb5
LA15
Ra15
Rb1
LA215
Ra15
Rb2
LA415
Ra15
Rb3
LA615
Ra15
Rb4
LA815
Ra15
Rb5
LA16
Ra16
Rb1
LA216
Ra16
Rb2
LA416
Ra16
Rb3
LA616
Ra16
Rb4
LA816
Ra16
Rb5
LA17
Ra17
Rb1
LA217
Ra17
Rb2
LA417
Ra17
Rb3
LA617
Ra17
Rb4
LA817
Ra17
Rb5
LA18
Ra18
Rb1
LA218
Ra18
Rb2
LA418
Ra18
Rb3
LA618
Ra18
Rb4
LA818
Ra18
Rb5
LA19
Ra19
Rb1
LA219
Ra19
Rb2
LA419
Ra19
Rb3
LA619
Ra19
Rb4
LA819
Ra19
Rb5
LA20
Ra20
Rb1
LA220
Ra20
Rb2
LA420
Ra20
Rb3
LA620
Ra20
Rb4
LA820
Ra20
Rb5
LA21
Ra21
Rb1
LA221
Ra21
Rb2
LA421
Ra21
Rb3
LA621
Ra21
Rb4
LA821
Ra21
Rb5
LA22
Ra22
Rb1
LA222
Ra22
Rb2
LA422
Ra22
Rb3
LA622
Ra22
Rb4
LA822
Ra22
Rb5
LA23
Ra23
Rb1
LA223
Ra23
Rb2
LA423
Ra23
Rb3
LA623
Ra23
Rb4
LA823
Ra23
Rb5
LA24
Ra24
Rb1
LA224
Ra24
Rb2
LA424
Ra24
Rb3
LA624
Ra24
Rb4
LA824
Ra24
Rb5
LA25
Ra25
Rb1
LA225
Ra25
Rb2
LA425
Ra25
Rb3
LA625
Ra25
Rb4
LA825
Ra25
Rb5
LA26
Ra26
Rb1
LA226
Ra26
Rb2
LA426
Ra26
Rb3
LA626
Ra26
Rb4
LA826
Ra26
Rb5
LA27
Ra27
Rb1
LA227
Ra27
Rb2
LA427
Ra27
Rb3
LA627
Ra27
Rb4
LA827
Ra27
Rb5
LA28
Ra28
Rb1
LA228
Ra28
Rb2
LA428
Ra28
Rb3
LA628
Ra28
Rb4
LA828
Ra28
Rb5
LA29
Ra29
Rb1
LA229
Ra29
Rb2
LA429
Ra29
Rb3
LA629
Ra29
Rb4
LA829
Ra29
Rb5
LA30
Ra30
Rb1
LA230
Ra30
Rb2
LA430
Ra30
Rb3
LA630
Ra30
Rb4
LA830
Ra30
Rb5
LA31
Ra31
Rb1
LA231
Ra31
Rb2
LA431
Ra31
Rb3
LA631
Ra31
Rb4
LA831
Ra31
Rb5
LA32
Ra32
Rb1
LA232
Ra32
Rb2
LA432
Ra32
Rb3
LA632
Ra32
Rb4
LA832
Ra32
Rb5
LA33
Ra33
Rb1
LA233
Ra33
Rb2
LA433
Ra33
Rb3
LA633
Ra33
Rb4
LA833
Ra33
Rb5
LA34
Ra34
Rb1
LA234
Ra34
Rb2
LA434
Ra34
Rb3
LA634
Ra34
Rb4
LA834
Ra34
Rb5
LA35
Ra35
Rb1
LA235
Ra35
Rb2
LA435
Ra35
Rb3
LA635
Ra35
Rb4
LA835
Ra35
Rb5
LA36
Ra36
Rb1
LA236
Ra36
Rb2
LA436
Ra36
Rb3
LA636
Ra36
Rb4
LA836
Ra36
Rb5
LA37
Ra37
Rb1
LA237
Ra37
Rb2
LA437
Ra37
Rb3
LA637
Ra37
Rb4
LA837
Ra37
Rb5
LA38
Ra38
Rb1
LA238
Ra38
Rb2
LA438
Ra38
Rb3
LA638
Ra38
Rb4
LA838
Ra38
Rb5
LA39
Ra39
Rb1
LA239
Ra39
Rb2
LA439
Ra39
Rb3
LA639
Ra39
Rb4
LA839
Ra39
Rb5
LA40
Ra40
Rb1
LA240
Ra40
Rb2
LA440
Ra40
Rb3
LA640
Ra40
Rb4
LA840
Ra40
Rb5
LA41
Ra41
Rb1
LA241
Ra41
Rb2
LA441
Ra41
Rb3
LA641
Ra41
Rb4
LA841
Ra41
Rb5
LA42
Ra42
Rb1
LA242
Ra42
Rb2
LA442
Ra42
Rb3
LA642
Ra42
Rb4
LA842
Ra42
Rb5
LA43
Ra43
Rb1
LA243
Ra43
Rb2
LA443
Ra43
Rb3
LA643
Ra43
Rb4
LA843
Ra43
Rb5
LA44
Ra44
Rb1
LA244
Ra44
Rb2
LA444
Ra44
Rb3
LA644
Ra44
Rb4
LA844
Ra44
Rb5
LA45
Ra45
Rb1
LA245
Ra45
Rb2
LA445
Ra45
Rb3
LA645
Ra45
Rb4
LA845
Ra45
Rb5
LA46
Ra46
Rb1
LA246
Ra46
Rb2
LA446
Ra46
Rb3
LA646
Ra46
Rb4
LA846
Ra46
Rb5
LA47
Ra47
Rb1
LA247
Ra47
Rb2
LA447
Ra47
Rb3
LA647
Ra47
Rb4
LA847
Ra47
Rb5
LA48
Ra48
Rb1
LA248
Ra48
Rb2
LA448
Ra48
Rb3
LA648
Ra48
Rb4
LA848
Ra48
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Ra83
Rb9
LA983
Ra83
Rb10
LA184
Ra84
Rb6
LA384
Ra84
Rb7
LA584
Ra84
Rb8
LA784
Ra84
Rb9
LA984
Ra84
Rb10
LA185
Ra85
Rb6
LA385
Ra85
Rb7
LA585
Ra85
Rb8
LA785
Ra85
Rb9
LA985
Ra85
Rb10
LA186
Ra86
Rb6
LA386
Ra86
Rb7
LA586
Ra86
Rb8
LA786
Ra86
Rb9
LA986
Ra86
Rb10
LA187
Ra87
Rb6
LA387
Ra87
Rb7
LA587
Ra87
Rb8
LA787
Ra87
Rb9
LA987
Ra87
Rb10
LA188
Ra88
Rb6
LA388
Ra88
Rb7
LA588
Ra88
Rb8
LA788
Ra88
Rb9
LA988
Ra88
Rb10
LA189
Ra89
Rb6
LA389
Ra89
Rb7
LA589
Ra89
Rb8
LA789
Ra89
Rb9
LA989
Ra89
Rb10
LA190
Ra90
Rb6
LA390
Ra90
Rb7
LA590
Ra90
Rb8
LA790
Ra90
Rb9
LA990
Ra90
Rb10
LA191
Ra91
Rb6
LA391
Ra91
Rb7
LA591
Ra91
Rb8
LA791
Ra91
Rb9
LA991
Ra91
Rb10
LA192
Ra92
Rb6
LA392
Ra92
Rb7
LA592
Ra92
Rb8
LA792
Ra92
Rb9
LA992
Ra92
Rb10
LA193
Ra93
Rb6
LA393
Ra93
Rb7
LA593
Ra93
Rb8
LA793
Ra93
Rb9
LA993
Ra93
Rb10
LA194
Ra94
Rb6
LA394
Ra94
Rb7
LA594
Ra94
Rb8
LA794
Ra94
Rb9
LA994
Ra94
Rb10
LA195
Ra95
Rb6
LA395
Ra95
Rb7
LA595
Ra95
Rb8
LA795
Ra95
Rb9
LA995
Ra95
Rb10
LA196
Ra96
Rb6
LA396
Ra96
Rb7
LA596
Ra96
Rb8
LA796
Ra96
Rb9
LA996
Ra96
Rb10
LA197
Ra97
Rb6
LA397
Ra97
Rb7
LA597
Ra97
Rb8
LA797
Ra97
Rb9
LA997
Ra97
Rb10
LA198
Ra98
Rb6
LA398
Ra98
Rb7
LA598
Ra98
Rb8
LA798
Ra98
Rb9
LA998
Ra98
Rb10
LA199
Ra99
Rb6
LA399
Ra99
Rb7
LA599
Ra99
Rb8
LA799
Ra99
Rb9
LA999
Ra99
Rb10
LA200
Ra100
Rb6
LA400
Ra100
Rb7
LA600
Ra100
Rb8
LA800
Ra100
Rb9
LA1000
Ra100
Rb10
wherein Rb1 to Rb10 have the following structures:
wherein Ra1 to Ra100 have the following structures:

### Claim 19 (depends on 8)

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.

### Claim 20 (depends on 8)

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.