Organic electroluminescent materials and devices

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 is an emissive layer and the compound of Formula I is a host compound of Formula I:
• wherein
• groups A, B, C, D, E, and F are independently selected from hydrogen, deuterium or a structure of Formula II, wherein four to six of the groups A to F are independently a structure of Formula II;
• T1, T2, T3, T4 and T5 are independently selected from N or CR, wherein no more than three of T1 to T5 can be N;
• wherein R is selected from the group consisting of hydrogen, deuterium, halogen, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
• wherein one at least one of T1, T2, T3, T4 and T5 represents N and at least one of R includes a polycyclic group;
• or
• each of T1, T2, T3, T4 and T5 represents CR and at least one R includes two polycyclic groups;
• wherein each polycyclic group is selected from the group consisting of (a) a group selected from the group consisting of
• wherein
• the polycyclic group is bonded to one of T2, T3, or T4 in Formula II through one of X1 to X30, one of L1 to L4, or one of Z1 and Z2;
• X1 to X30 are independently selected from the group consisting of N and CRX, but no single 6-membered aromatic ring can have more than three N;
• wherein RX is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, deuterated alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
• Y is selected from the group consisting of C and Si;
• Z1 and Z2 are independently selected from the group consisting of NR, BR, N, O, S, Se, CR1R2, SiR1R2, and GeR1R2;
• wherein R1 and R2 are independently selected from the group consisting of deuterium, alkyl, aryl, heteroaryl, and combinations thereof;
• L1, L2, L3, and L4 are independently selected from the group consisting of O, S, BR, NR, CR1R2 and SiR1R2;
• (b)
• wherein
• X1 to X8 are independently selected from the group consisting of N and CRX, but no single 6-membered aromatic ring can have more than three N;
• wherein RX is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, deuterated alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
• the polycyclic group is bonded to one of T2, T3, or T4 in Formula II through one of X1 to X8;
• Z1 is selected from the group consisting of, BR, NR, O, S, Se, CR1R2, SiR1R2, and GeR1R2;
• provided that when Z1 is O or S, then at least one of X1 to X8 is N;
• and
• R1 and R2 are independently selected from the group consisting of deuterium, alkyl, aryl, heteroaryl, and combinations thereof;
• (c)
• wherein
• the polycyclic group is bonded to one of T2, T3, or T4 in Formula II through Z1;
• Z1 is N;
• X1 to X8 are independently selected from the group consisting of N and CRX, but no single 6-membered aromatic ring can have more than three N;
• wherein RX is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, deuterated alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
• and
• at least one RX is heteroaryl;
• (d)
• wherein
• the polycyclic group is bonded to one of T2, T3, or T4 in Formula II through one of X1 to X8 or one of Z1 and Z2;
• X1 to X8 are independently selected from the group consisting of N and CRX, but no single 6-membered aromatic ring can have more than three N;
• wherein RX is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, deuterated alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
• Z1 is NR or N,
• wherein when Z1 is NR, Z2 is selected from the group consisting of NR, BR, N, O, S, Se, CR1R2, SiR1R2, and GeR1R2;
• wherein when Z1 is N, Z2 is selected from the group consisting of NR, BR, N, Se, CR1R2, SiR1R2, and GeR1R2;
• and
• R1 and R2 are independently selected from the group consisting of deuterium, aryl, heteroaryl, and combinations thereof;
• (e)
• wherein
• the polycyclic group is bonded to one of T2, T3, or T4 in Formula II through one of X1 to X8 or one of Z1 and Z2;
• X1 to X8 are independently selected from the group consisting of N and CRX, but no single 6-membered aromatic ring can have more than three N;
• wherein RX is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, deuterated alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
• Z1 and Z2 are independently selected from the group consisting of BR, O, S, Se, CR1R2, SiR1R2, and GeR1R2;
• and
• R1 and R2 are independently selected from the group consisting of deuterium, alkyl, aryl, heteroaryl, and combinations thereof;
• and
• (f)
• wherein
• the polycyclic group is bonded to one of T2, T3, or T4 in Formula II through one of X1 to X8 or one of Z1 and Z2;
• X1 to X8 are independently selected from the group consisting of N and CRX, but no single 6-membered aromatic ring can have more than three N;
• wherein RX is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, deuterated alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
• Z1 and Z2 are independently selected from the group consisting of NR, BR, N, O, S, Se, CR1R2, SiR1R2, and GeR1R2;
• wherein R1 and R2 are independently selected from the group consisting of deuterium, alkyl, aryl, heteroaryl, and combinations thereof;
• provided that when one of Z1 and Z2 is N, then the other of Z1 and Z2 is not O.

A consumer product comprising an organic light-emitting device comprising:

• an anode;
• a cathode;
• and an organic layer disposed between the anode and the cathode, the organic layer comprising a compound of Formula I:
• wherein
• groups A, B, C, D, E, and F are independently selected from hydrogen, deuterium or a structure of Formula II, wherein four to six of the groups A to F are independently a structure of Formula II;
• T1, T2, T3, T4 and T5 are independently selected from N or CR, wherein no more than three of T1 to T5 can be N;
• wherein R is selected from the group consisting of hydrogen, deuterium, halogen, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
• wherein at least one of T1, T2, T3, T4 and T5 represents N and at least one of R includes a polycyclic group;
• or
• each of T1, T2, T3, T4 and T5 represents CR and at least one R includes two polycyclic groups;
• wherein each the at least one polycyclic group is selected from the group consisting of (a) a group selected from the group consisting of
• wherein
• the polycyclic group is bonded to one of T2, T3, or T4 in Formula II through one of X1 to X30, one of L1 to L4, or one of Z1 and Z2;
• X1 to X30 are independently selected from the group consisting of N and CRX, but no single 6-membered aromatic ring can have more than three N;
• wherein RX is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, deuterated alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
• Y is selected from the group consisting of C and Si;
• Z1 and Z2 are independently selected from the group consisting of NR, BR, N, O, S, Se, CR1R2, SiR1R2, and GeR1R2;
• wherein R1 and R2 are independently selected from the group consisting of deuterium, alkyl, aryl, heteroaryl, and combinations thereof;
• L1, L2, L3, and L4 are independently selected from the group consisting of O, S, BR, NR, CR1R2 and SiR1R2;
• (b)
• wherein
• X1 to X8 are independently selected from the group consisting of N and CRX, but no single 6-membered aromatic ring can have more than three N;
• wherein RX is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, deuterated alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
• the polycyclic group is bonded to one of T2, T3, or T4 in Formula II through one of X1 to X8;
• Z1 is selected from the group consisting of, BR, NR, O, S, Se, CR1R2, SiR1R2, and
• GeR1R2;
• provided that when Z1 is O or S, then at least one of X1 to X8 is N;
• and
• R1 and R2 are independently selected from the group consisting of deuterium, alkyl, aryl, heteroaryl, and combinations thereof;
• (c)
• wherein
• the polycyclic group is bonded to one of T2, T3, or T4 in Formula II through Z1;
• Z1 is N;
• X1 to X8 are independently selected from the group consisting of N and CRX, but no single 6-membered aromatic ring can have more than three N;
• wherein RX is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, deuterated alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
• and
• at least one RX is heteroaryl;
• (d)
• wherein
• the polycyclic group is bonded to one of T2, T3, or T4 in Formula II through one of X1 to X8 or one of Z1 and Z2;
• X1 to X8 are independently selected from the group consisting of N and CRX, but no single 6-membered aromatic ring can have more than three N;
• wherein RX is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, deuterated alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
• Z1 is NR or N,
• wherein when Z1 is NR, Z2 is selected from the group consisting of NR, BR, N, O, S, Se, CR1R2, SiR1R2, and GeR1R2;
• wherein when Z1 is N, Z2 is selected from the group consisting of NR, BR, N, Se, CR1R2, SiR1R2, and GeR1R2;
• and
• R1 and R2 are independently selected from the group consisting of deuterium, aryl, heteroaryl, and combinations thereof;
• (e)
• wherein
• the polycyclic group is bonded to one of T2, T3, or T4 in Formula II through one of X1 to X8 or one of Z1 and Z2;
• X1 to X8 are independently selected from the group consisting of N and CRX, but no single 6-membered aromatic ring can have more than three N;
• wherein RX is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, deuterated alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
• Z1 and Z2 are independently selected from the group consisting of BR, O, S, Se, CR1R2, SiR1R2, and GeR1R2;
• and
• R1 and R2 are independently selected from the group consisting of deuterium, alkyl, aryl, heteroaryl, and combinations thereof;
• and
• (f)
• wherein
• the polycyclic group is bonded to one of T2, T3, or T4 in Formula II through one of X1 to X8 or one of Z1 and Z2;
• X1 to X8 are independently selected from the group consisting of N and CRX, but no single 6-membered aromatic ring can have more than three N;
• wherein RX is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, deuterated alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
• Z1 and Z2 are independently selected from the group consisting of NR, BR, N, O, S, Se, CR1R2, SiR1R2, and GeR1R2;
• wherein R1 and R2 are independently selected from the group consisting of deuterium, alkyl, aryl, heteroaryl, and combinations thereof;
• provided that when one of Z1 and Z2 is N, then the other of Z1 and Z2 is not O.