Organic electroluminescent materials and devices
A novel compound having a benzimidazole based structure is disclosed that is selected from one of the following structures: The compound is useful in improving photophysical performance of OLEDs.
1. A compound selected from the group consisting of:
wherein,
A, B, C, D, and F are each independently a 5-membered or 6-membered aromatic ring;
ring B may or may not be present;
M is selected from the group consisting of Pt, Pd, Cu, and Au;
Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , Z 6 , Z 6′ , Z 7 and Z 7′ are each independently selected from the group consisting of C and N;
wherein one of Z 6′ and Z 7′ is a neutral carbene carbon, and the other one of Z 6′ and Z 7′ is an anionic carbon;
m1, m2 and m3 are each independently an integer of 0 or 1; when m2 is 0, each m1 and m3 is 1: when m2 is 1, each m1 and m3 can be 0 or 1;
when m1 is 0, L 1 is not present; when m2 is 0, L 2 is not present; when m3 is 0, L 3 is not present;
L 1 , L 2 , and L 3 each independently selected from the group consisting of a direct bond, BR, NR, PR, O, S, Se, C═O, S═O, SO 2 , CRR′, SiRR′, GeRR′, alkyl, cycloalkyl, and combinations thereof;
each R A , R B , R C , R D , and R E represents mono- to maximum possible number of substitutions, or no substitution;
each R A , R B , R C , R D , R E , R and R′ is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, boryl, and combinations thereof,
R 1 is selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and
any two substituents can be joined or fused into a ring, provided that, in Formula I, if ring C is a 5-membered aromatic ring, L 2 is present and is a direct bond, then at least one pair of R D , one pair of R E , or one R D and one R E are joined together to form a fused ring.
2. The compound of claim 1 , wherein M is Pt.
3. The compound of claim 1 , wherein one of Z 6 and Z 7 is nitrogen, and the other one of Z 6 and Z 7 is carbon.
4. The compound of claim 1 , wherein rings A, B, C, D, and F are each independently selected from the group consisting of phenyl, pyridine, pyrimidine, triazine, pyrazole, triazole, imidazole, and imidazole derived carbene.
5. The compound of claim 1 , wherein L 3 and Z 4 are fused to form a 5-membered or 6-membered carbocyclic or heterocyclic ring.
6. The compound of claim 1 , wherein L 3 is present and is selected from the group consisting of O, S, and CRR′.
7. The compound of claim 1 , wherein the compound is Formula I and ring A is pyridine with N coordinating to M.
8. The compound of claim 1 , wherein the compound is selected from the group consisting of:
wherein,
Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , Z 6 , Z 6′ , Z 7 , Z 7′ , Z 8 , Z 9 , Z 10 , Z 11 , Z 12 , and Z 13 are each independently C or N;
wherein in rings C and D:
one of Z 6′ and Z 7′ is a neutral carbene carbon, and the other one of Z 6′ and Z 7′ is an anionic carbon;
one of Z 10 and Z 11 is a neutral carbene carbon, and the other one of Z 10 and Z 11 is an anionic carbon;
one of Z 12 and Z 13 is a neutral carbene carbon, and the other one of Z 12 and Z 13 is an anionic carbon;
one of Z 14 and Z 15 is a neutral carbene carbon, and the other one of Z 14 and Z 15 is an anionic carbon;
R F represents mono- to maximum possible number of substitutions, or no substitution; and
each R F is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, boryl, and combinations thereof, and any two substituents can be joined or fused into a ring.
9. The compound of claim 8 , wherein the compound has the structure:
wherein R Y represents mono- to tetra-substitutions, or no substitution;
wherein any two substituents can be joined or fused into a ring;
wherein R Y is a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, boryl, and combinations thereof, and
wherein R Z is selected from the group consisting of alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, silyl, aryl, heteroaryl, boryl, partially or fully deturated variants thereof, partially or fully fluorinated variants thereof, and combinations thereof.
10. The compound of claim 1 , wherein at least one of R A , R B , R C , R D , R E , R F , R and R′ comprises a chemical group containing at least three 6-membered aromatic rings that are not fused next to each other.
11. The compound of claim 9 , wherein at least one of R Y and R Z comprises a chemical group containing at least three 6-membered aromatic rings that are not fused next to each other.
12. The compound of claim 1 , wherein the compound is the compound x having the formula (L Xi )Pt(L Yj )(L Zk );
wherein,
L Xi is a bidentate ligand;
L Yj is a monodentate ligand;
L Zk is a monodentate ligand;
L Xi is linked to L Zk by a linking group L 3 ;
L Zk is linked to L Yj by a direct bond;
x=30(k−1)+j+1200(i−1), i is an integer from 1 to 212190, 212216 to 212219, 212231 to 212234, j is an integer from 1 to 30, and k is an integer from 1 to 40; when k=41, 42, or 43, x=25(k−41)+j+75(i−1)+254709600, i is an integer from 1 to 212190, 212216 to 212219, 212231 to 212234, j is an integer from 1 to 25;
L Xi is selected from the group consisting of L X1 to L X212190 , L X212216 to L X212219 , and L X212231 to L X212234 whose structures are defined as follows:
L Xi
Structure of L Xi
Ar 1 , R 1
i
wherein L X1 to L X9900 have the structure
wherein Ar 1 = A m and R 1′ = R n , wherein m is an integer from 1 to 30 and n is an integer from 1 to 330, and
y = 330( m − 1) + n
wherein L X9901 -L X19800 have the structure
wherein Ar 1 = A m and R 1′ = R n , wherein m is an integer from 1 to 30 and n is an integer from 1 to 330, and
y = 330( m − 1) + n + 9900
wherein L X19801 -L X29700 have the structure
wherein Ar 1 = A m and R 1′ = R n , wherein m is an integer from 1 to 30 and n is an integer from 1 to 330, and
y = 330( m − 1) + n + 19800
wherein L X29701 -L X39600 have the structure
wherein Ar 1 = A m and R 1′ = R n , wherein m is an integer from 1 to 30 and n is an integer from 1 to 330, and
y = 330( m − 1) + n + 29700
wherein L X39601 -L X49500 have the structure
wherein Ar 1 = A m and R 1′ = R n , wherein m is an integer from 1 to 30 and n is an integer from 1 to 330, and
y = 330( m − 1) + n + 39600
wherein L X49501 -L X59400 have the structure
wherein Ar 1 = A m and R 1′ = R n , wherein m is an integer from 1 to 30 and n is an integer from 1 to 330, and
y = 330( m − 1) + n + 49500
wherein L X59401 -L X69300 have the structure
wherein Ar 1 = A m and R 1′ = R n , wherein m is an integer from 1 to 30 and n is an integer from 1 to 330, and
y = 330( m − 1) + n + 59400
wherein L X69301 -L X79200 have the structure
wherein Ar 1 = A m and R 1′ = R n , wherein m is an integer from 1 to 30 and n is an integer from 1 to 330, and
y = 330( m − 1) + n + 69300
wherein L X79201 to L X79530 have the structure
wherein R 1′ = R n , wherein n is an integer from 1 to 330, and
y = n + 79200
wherein L X79531- L X79860 have the structure
wherein R 1′ = R n , wherein n is an integer from 1 to 330, and
y = n + 79530
wherein L X79861 -L X80190 have the structure
wherein R 1′ = R n , wherein n is an integer from 1 to 330, and
y = n + 79860
wherein L X80191 -L X80520 have the structure
wherein R 1′ = R n , wherein n is an integer from 1 to 330, and
y = n + 80190
wherein L X80521 to L X90420 have the structure
wherein Ar 1 = A m and R 1′ = R n , wherein m is an integer from 1 to 30 and n is an integer from 1 to 330, and
y = 330( m − 1) + n + 80520
wherein L X90421 to L X100320 have the structure
wherein Ar 1 = A m and R 1′ = R n , wherein m is an integer from 1 to 30 and n is an integer from 1 to 330, and
y = 330( m − 1) + n + 90420
wherein L X100321 to L X110220
wherein Ar 1 = A m and R 1′ = R n , wherein m is an integer from 1 to 30 and n is an have the structure integer from 1 to 330, and
y = 330( m − 1) + n + 100320
wherein L X110221 to L X120120 have the structure
wherein Ar 1 = A m and R 1′ = R n , wherein m is an integer from 1 to 30 is an integer integer from 1 to 330, and
y = 330( m − 1) + n + 110220
wherein L X120121 to L X130020 have the structure
wherein Ar 1 = A m and R 1′ = R n , wherein m is an integer from 1 to 30 and n is an integer from 1 to 330, and
y = 330( m − 1) + n + 120120
wherein L X130021 to L X139920 have the structure
wherein Ar 1 = A m and R 1′ = R n , wherein m is an integer from 1 to 30 and n is an integer from 1 to 330, and
y = 330( m − 1) + n + 130020
wherein L X139921 to L X149820 have the structure
wherein Ar 1 = A m and R 1′ = R n , wherein m is an integer from 1 to 30 and n is an integer from 1 to 330, and
y = 330( m − 1) + n + 139920
wherein L X149821 to L X159720 have the structure
wherein Ar 1 = A m and R 1′ = R n , wherein m is an integer from 1 to 30 and n is an integer from 1 to 330, and
y = 330( m − 1) + n + 149820
wherein L X159721 to L X169620 have the structure
wherein Ar 1 = A m and R 1′ = R n , wherein m is an integer from 1 to 30 and n is an integer from 1 to 330, and
y = 330( m − 1) + n + 159720
wherein L X169621 to L X169950 have the structure
wherein R 1′ = R n , wherein n is an integer from 1 to 330, and
y = n + 169620
wherein L X169951 to L X170280 have the structure
wherein R 1′ = R n , wherein n is an integer from 1 to 330, and
y = n + 169950
wherein L X170281 to L X170610 have the structure
wherein R 1′ = R n , wherein n is an integer from 1 to 330, and
y = n + 170280
wherein L X170610 to L X170940 have the structure
wherein R 1′ = R n , wherein n is an integer from 1 to 330, and
y = n + 170610
wherein L X170941 to L X171270 have the structure
wherein R 1′ = R n , wherein n is an integer from 1 to 330, and
y = n + 170940
wherein L X171271 to L X171600 have the structure
wherein R 1′ = R n , wherein n is an integer from 1 to 330, and
y = n + 171270
wherein L X171601 to L X181500 have the structure
wherein Ar 1 = A m and R 1′ = R n , wherein m is an integer from 1 to 30 and n is an integer from 1 to 330, and
y = 330( m − 1) + n + 171600
wherein L X181501 to L X191400 have the structure
wherein Ar 1 = A m and R 1′ = R n , wherein m is an integer from 1 to 30 and n is an integer from 1 to 330, and
y = 330( m − 1) + n + 181500
wherein L X191401 to L X191730 have the structure
wherein R 1′ = R n , wherein n is an integer from 1 to 330, and
y = n + 191400
wherein L X191731 to L X192060 have the structure
wherein R 1′ = R n , wherein n is an integer from 1 to 330, and
y = n + 191730
wherein L X192061 to L X201960 have the structure
wherein Ar 1 = A m and R 1′ = R n , wherein m is an integer from 1 to 30 and n is an integer from 1 to 330, and
y = 330( m − 1) + n + 192060
wherein L X201961 to L X211860 have the structure
wherein Ar 1 = A m and R 1′ = R n , wherein m is an integer from 1 to 30 and n is an integer from 1 to 330, and
y = 330( m − 1) + n + 201960
wherein L X211861 to L X212190 have the structure
wherein R 1′ = R n , wherein n is an integer from 1 to 330, and
y = n + 211860
wherein A1 to A30 have the following structures:
and R1 to R330 have the following structures:
L Yj is selected from the group consisting of:
L Zk is selected from the group consisting of:
and the * of L Zk attaches to the * of L Xi , and the ** of L Zk attaches to the ** of L Yj .
13. The compound of claim 12 , wherein x=5(k−41)+(j−25)+15(i−1)+270628950, i is an integer from 1 to 212190, 212216 to 212219, 212231 to 212234, j is an integer from 26 to 30, and k is an integer from 41 to 43.
14. The compound of claim 1 , wherein the compound is selected from the group consisting of:
15. An organic light emitting device (OLED) comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising a compound selected from the group consisting of:
wherein,
A, B, C, D, and F are each independently a 5-membered or 6-membered aromatic ring;
ring B may or may not be present;
M is selected from the group consisting of Pt, Pd, Cu, and Au;
Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , Z 6 , Z 6′ , Z 7 and Z 7′ are each independently selected from the group consisting of C and N;
wherein one of Z 6′ and Z 7′ is a neutral carbene carbon, and the other one of Z 6′ and Z 7′ is an anionic carbon;
m1, m2 and m3 are each independently an integer of 0 or 1; when m2 is 0, each m1 and m3 is 1;
when m2 is 1, each m1 and m3 can be 0 or 1;
when m1 is 0, L 1 is not present; when m2 is 0, L 2 is not present; when m3 is 0, L 3 is not present;
L 1 , L 2 , and L 3 each independently selected from the group consisting of a direct bond, BR, NR, PR, O, S, Se, C═O, S═O, SO 2 , CRR′, SiRR′, GeRR′, alkyl, cycloalkyl, and combinations thereof;
each R A , R B , R C , R D , and R E represents mono- to maximum possible number of substitutions, or no substitution;
each R A , R B , R C , R D , R E , R and R′ is a hydrogen or a substituent independently selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, boryl, and combinations thereof;
R 1 is selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and
any two substituents can be joined or fused into a ring, provided that, in Formula I, if ring C is a 5-membered aromatic ring, L 2 is present and is a direct bond, then at least one pair of R D , one pair of R E , or one R D and one R E are joined together to form a fused ring.
16. The OLED of claim 15 , wherein the organic layer further comprises a host, wherein the host comprises at least one chemical group selected from the group consisting of triphenylene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, azatriphenylene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.
17. The OLED of claim 16 , wherein the host is selected from the group consisting of:
and combinations thereof.
18. The OLED of claim 15 , wherein the compound is a sensitizer; wherein the device further comprises an acceptor; and wherein the acceptor is selected from the group consisting of fluorescent emitter, delayed fluorescence emitter, and combination thereof.
19. 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, comprising a compound selected from the group consisting of:
wherein,
A, B, C, D, and F are each independently a 5-membered or 6-membered aromatic ring;
ring B may or may not be present;
M is selected from the group consisting of Pt, Pd, Cu, and Au;
Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , Z 6 , Z 6′ , Z 7 and Z 7′ are each independently selected from the group consisting of C and N;
wherein one of Z 6′ and Z 7′ is a neutral carbene carbon, and the other one of Z 6′ and Z 7′ is an anionic carbon;
m1, m2 and m3 are each independently an integer of 0 or 1; when m2 is 0, each m1 and m3 is 1; when m2 is 1, each m1 and m3 can be 0 or 1;
when m1 is 0, L 1 is not present; when m2 is 0, L 2 is not present; when m3 is 0, L 3 is not present;
L 1 , L 2 , and L 3 each independently selected from the group consisting of a direct bond, BR, NR, PR, O, S, Se, C═O, S═O, SO 2 , CRR′, SiRR′, GeRR′, alkyl, cycloalkyl, and combinations thereof;
each R A , R B , R C , R D , and R E represents mono- to maximum possible number of substitutions, or no substitution;
each R A , R B , R C , R D , R E , R and R′ is a hydrogen or a substituent independently selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, boryl, and combinations thereof;
R 1 is selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and
any two substituents can be joined or fused into a ring, provided that, in Formula I, if ring C is a 5-membered aromatic ring, L 2 is present and is a direct bond, then at least one pair of R D , one pair of R E , or one R D and one R E are joined together to form a fused ring.
20. The compound of claim 1 , wherein Z 6′ is a neutral carbene carbon, and Z 7′ is an anionic carbon.