IP Library › Granted Patent US 9,397,302
Granted Patent B2
US 9,397,302 · App. 14/509,274 · Granted Jul 19, 2016

Organic electroluminescent materials and devices

Inventors: Pierre-Luc T. Boudreault (Pennington, NJ); Walter Yeager (Yardley, PA); Chuanjun Xia (Lawrenceville, NJ)
Assignee: Universal Display Corporation
H01L51/0085C07F15/0033H01L51/5016
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Quick Facts
Patent No.
US 9,397,302
App. No.
14/509,274
Filed
Oct 8, 2014
Granted
Jul 19, 2016
Kind
B2
Art Unit
2894
USPC
257/40
Abstract

Novel ligands for metal complex compounds that are useful as a phosphorescent emitter in organic light emitting devices that incorporate fluorinated side chains in the ligands are disclosed. Such metal complex has at least one substituent R selected from the group consisting of partially fluorinated alkyl, partially fluorinated cycloalkyl, and combinations thereof, wherein R is directly bonded to an aromatic ring, In the compound, C having an F attached thereto is separated by at least one carbon atom from the aromatic ring.

Claims (608)

1. A composition comprising a first compound;

wherein the first compound is capable of functioning as a phosphorescent emitter in an organic light emitting device at room temperature;

wherein the first compound has at least one aromatic ring and at least one substituent R;

wherein each of the at least one R is independently selected from the group consisting of partially fluorinated alkyl, partially fluorinated cycloalkyl, and combinations thereof;

wherein each of the at least one R is directly bonded to one of the aromatic rings;

wherein in each of the at least one R, C having an F attached thereto is separated by at least one carbon atom from the aromatic ring;

wherein the first compound 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;

wherein x is 1, 2, or 3;

wherein y is 0, 1, or 2;

wherein z is 0, 1, or 2;

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

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

wherein R a , R b , R c , and R d independently represent mono, di, tri, or tetra substitution, or no substitution;

wherein R a , R b , R c , and R d are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;

wherein two adjacent substituents of R a , R b , R c , and R d are optionally joined to form a ring or form a multidentate ligand; and

wherein at least one of the R a , R b , R c , and R d includes at least one R.

2. The composition of claim 1 , wherein the first compound is capable of emitting light from a triplet excited state to a ground singlet state at room temperature.

3. The composition of claim 1 , wherein the metal is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu.

4. The composition of claim 1 , wherein the metal is Ir.

5. The composition of claim 1 , wherein the metal is Pt.

6. The composition of claim 1 , wherein the C having an F attached thereto is separated by at least two carbon atoms from the aromatic ring.

7. The composition of claim 1 , wherein the C having an F attached thereto is separated by at least three carbon atoms from the aromatic ring.

8. The composition of claim 1 , wherein each of the at least one R contains at least one CF 3 group.

9. The composition of claim 1 , wherein none of the at least one R contain any CF 3 groups.

10. The composition of claim 1 , wherein the first compound does not have any F atoms other than in the at least one R.

11. The composition of claim 1 , wherein the aromatic ring comprises LUMO electron density of the first compound.

12. The composition of claim 1 , wherein the first compound has the formula of Ir(L 1 ) 2 (L 2 ).

13. The composition of claim 12 , wherein L 1 has the formula selected from the group consisting of:

and

wherein L 2 has the formula:

14. The composition of claim 13 , wherein L 2 has the formula:

wherein R e , R f , R h , and R i are independently selected from group consisting of alkyl, cycloalkyl, aryl, and heteroaryl;

wherein at least one of R e , R f , R h , and R i has at least two carbon atoms;

wherein R g is selected from group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

15. The composition of claim 12 , wherein L 1 and L 2 are different and each independently selected from the group consisting of:

16. The composition of claim 12 , wherein L 1 and L 2 are each independently selected from the group consisting of:

17. The composition of claim 1 , wherein the first compound has the formula of Pt(L 1 ) 2 or Pt(L 1 )(L 2 ).

18. The composition of claim 17 , wherein L 1 is connected to the other L 1 or L 2 to form a tetradentate ligand.

19. The composition of claim 1 , wherein at least one of R a , R b , R c , and R d includes an alkyl or cycloalkyl group that includes CD, CD 2 , or CD 3 , wherein D is deuterium.

20. The composition of claim 1 , wherein L 1 , L 2 , and L 3 are each independently selected from the group consisting of:

L A1 through L A41 , each

L A42 through L A82 , each

L A83 through L A123 , each

represented by the formula

represented by the formula

repesented by the formula

wherein

wherein

wherein

in L A1 , R = R A1 , in L A2 , R = R A2 ,

in L A42 , R = R A1 , in L A43 , R = R A2 ,

in L A83 , R = R A1 , in L A84 , R = R A2 ,

in L A3 , R = R A3 , in L A4 , R = R A4 ,

in L A44 , R = R A3 , in L A45 , R = R A4 ,

in L A85 , R = R A3 , in L A86 , R = R A4 ,

in L A5 , R = R A5 , in L A6 , R = R A6 ,

in L A46 , R = R A5 , in L A47 , R = R A6 ,

in L A87 , R = R A5 , in L A88 , R = R A6 ,

in L A7 , R = R A7 , in L A8 , R = R A8 ,

in L A48 , R = R A7 , in L A49 , R = R A8 ,

in L A89 , R = R A7 , in L A90 , R = R A8 ,

in L A9 , R = R A9 , in L A10 , R = R A10 ,

in L A50 , R = R A9 , in L A51 , R = R A10 ,

in L A91 , R = R A9 , in L A92 , R = R A10 ,

in L A11 , R = R A11 , in L A12 , R = R A12 ,

in L A52 , R = R A11 , in L A53 , R = R A12 ,

in L A93 , R = R A11 , in L A94 , R = R A12 ,

in L A13 , R = R A13 , in L A14 , R = R A14 ,

in L A54 , R = R A13 , in L A55 , R = R A14 ,

in L A95 , R = R A13 , in L A96 , R = R A14 ,

in L A15 , R = R A15 , in L A16 , R = R A16 ,

in L A56 , R = R A15 , in L A57 , R = R A16 ,

in L A97 , R = R A15 , in L A98 , R = R A16 ,

in L A17 , R = R A17 , in L A18 , R = R A18 ,

in L A58 , R = R A17 , in L A59 , R = R A18 ,

in L A99 , R = R A17 , in L A100 , R = R A18 ,

in L A19 , R = R A19 , in L A20 , R = R A20 ,

in L A60 , R = R A19 , in L A61 , R = R A20 ,

in L A101 , R = R A19 , in L A102 , R = R A20 ,

in L A21 , R = R A21 , in L A22 , R = R A22 ,

in L A62 , R = R A21 , in L A63 , R = R A22 ,

in L A103 , R = R A21 , in L A104 , R = R A22 ,

in L A23 , R = R A23 , in L A24 , R = R A24 ,

in L A64 , R = R A23 , in L A65 , R = R A24 ,

in L A105 , R = R A23 , in L A106 , R = R A24 ,

in L A25 , R = R A25 , in L A26 , R = R A26 ,

in L A66 , R = R A25 , in L A67 , R = R A26 ,

in L A107 , R = R A25 , in L A108 , R = R A26 ,

in L A27 , R = R A27 , in L A28 , R = R A28 ,

in L A68 , R = R A27 , in L A69 , R = R A28 ,

in L A109 , R = R A27 , in L A110 , R = R A28 ,

in L A29 , R = R A29 , in L A30 , R = R A30 ,

in L A70 , R = R A29 , in L A71 , R = R A30 ,

in L A111 , R = R A29 , in L A112 , R = R A30 ,

in L A31 , R = R A31 , in L A32 , R = R A32 ,

in L A72 , R = R A31 , in L A73 , R = R A32 ,

in L A113 , R = R A31 , in L A114 , R = R A32 ,

in L A33 , R = R A33 , in L A34 , R = R A34 ,

in L A74 , R = R A33 , in L A75 , R = R A34 ,

in L A115 , R = R A33 , in L A116 , R = R A34 ,

in L A35 , R = R A35 , in L A36 , R = R A36 ,

in L A76 , R = R A35 , in L A77 , R = R A36 ,

in L A117 , R = R A35 , in L A118 , R = R A35 ,

in L A37 , R = R A37 , in L A38 , R = R A38 ,

in L A78 , R = R A37 , in L A79 , R = R A38 ,

in L A119 , R = R A37 , in L A120 , R = R A38 ,

in L A39 , R = R A39 , in L A40 , R = R A40 ,

in L A80 , R = R A39 , in L A81 , R = R A40 ;

in L A121 , R = R A39 , in L A122 , R = R A40 ,

and in L A41 , R = R A41 ;      ,

and in L A82 , R = R A41 ;      ,

and in L A123 , R = R A41 ;      ,

L A124 through L A164 , each

L A165 through L A205 , each

L A206 through L A246 , each

represented by the formula

represented by the formula

repesented by the formula

wherein

wherein

wherein

in L A124, R = R A1 , in L A125 , R = R A2 ,

in L A165, R = R A1 , in L A166, R = R A2 ,

in L A206, R = R A1 , in L A207, R = R A2 ,

in L A126, R = R A3 , in L A127 , R = R A4 ,

in L A167, R = R A3 , in L A168, R = R A4 ,

in L A208, R = R A3 , in L A209, R = R A4 ,

in L A128, R = R A5 , in L A129 , R = R A6 ,

in L A169, R = R A5 , in L A170, R = R A6 ,

in L A210, R = R A5 , in L A211, R = R A6 ,

in L A130, R = R A7 , in L A131 , R = R A8 ,

in L A171, R = R A7 , in L A172, R = R A8 ,

in L A212, R = R A7 , in L A213, R = R A8 ,

in L A132, R = R A9 , in L A133 , R = R A10 ,

in L A173, R = R A9 , in L A174, R = R A10 ,

in L A214, R = R A9 , in L A215, R = R A10 ,

in L A134, R = R A11 , in L A135 , R = R A12 ,

in L A175, R = R A11 , in L A176, R = R A12 ,

in L A216, R = R A11 , in L A217, R = R A12 ,

in L A136, R = R A13 , in L A137 , R = R A14 ,

in L A177, R = R A13 , in L A178, R = R A14 ,

in L A218, R = R A13 , in L A219, R = R A14 ,

in L A138, R = R A15 , in L A139 , R = R A16 ,

in L A179, R = R A15 , in L A180, R = R A16 ,

in L A220, R = R A15 , in L A221, R = R A16 ,

in L A140, R = R A17 , in L A141 , R = R A18 ,

in L A181, R = R A17 , in L A182, R = R A18 ,

in L A222, R = R A17 , in L A223, R = R A18 ,

in L A142, R = R A19 , in L A143 , R = R A20 ,

in L A183, R = R A19 , in L A184, R = R A20 ,

in L A224, R = R A19 , in L A225, R = R A20 ,

in L A144, R = R A21 , in L A145 , R = R A22 ,

in L A185, R = R A21 , in L A186, R = R A22 ,

in L A226, R = R A21 , in L A227, R = R A22 ,

in L A146, R = R A23 , in L A147 , R = R A24 ,

in L A187, R = R A23 , in L A188, R = R A24 ,

in L A228, R = R A23 , in L A229, R = R A24 ,

in L A148, R = R A25 , in L A149 , R = R A26 ,

in L A189, R = R A25 , in L A190, R = R A26 ,

in L A230, R = R A25 , in L A231, R = R A26 ,

in L A150, R = R A27 , in L A151 , R = R A28 ,

in L A191, R = R A27 , in L A192, R = R A28 ,

in L A232, R = R A27 , in L A233, R = R A28 ,

in L A152, R = R A29 , in L A153 , R = R A30 ,

in L A193, R = R A29 , in L A194, R = R A30 ,

in L A234, R = R A29 , in L A235, R = R A30 ,

in L A154, R = R A31 , in L A155 , R = R A32 ,

in L A195, R = R A31 , in L A196, R = R A32 ,

in L A236, R = R A31 , in L A237, R = R A32 ,

in L A156, R = R A33 , in L A157 , R = R A34 ,

in L A197, R = R A33 , in L A198, R = R A34 ,

in L A238, R = R A33 , in L A239, R = R A34 ,

in L A158, R = R A35 , in L A159 , R = R A36 ,

in L A199, R = R A35 , in L A200, R = R A36 ,

in L A240, R = R A35 , in L A241, R = R A35 ,

in L A160, R = R A37 , in L A161 , R = R A38 ,

in L A201, R = R A37 , in L A202, R = R A38 ,

in L A242, R = R A37 , in L A243, R = R A38 ,

in L A162, R = R A39 , in L A163 , R = R A40 ,

in L A203, R = R A39 , in L A204, R = R A40 ;

in L A244, R = R A39 , in L A245, R = R A40 ,

and in L A164 , R = R A41 ;      ,

and in L A205 , R = R A41 ;      ,

and in L A246 , R = R A41 ;      ,

L A247 through L A287 , each

L A288 through L A328 , each

L A329 through L A369 , each

represented by the formula

represented by the formula

repesented by the formula

wherein

wherein

wherein

in L A247, R = R A1 , in L A248 , R = R A2 ,

in L A288, R = R A1 , in L A289, R = R A2 ,

in L A329, R = R A1 , in L A330, R = R A2 ,

in L A249, R = R A3 , in L A250 , R = R A4 ,

in L A290, R = R A3 , in L A291, R = R A4 ,

in L A331, R = R A3 , in L A332, R = R A4 ,

in L A251, R = R A5 , in L A252 , R = R A6 ,

in L A292, R = R A5 , in L A293, R = R A6 ,

in L A333, R = R A5 , in L A334, R = R A6 ,

in L A253, R = R A7 , in L A254 , R = R A8 ,

in L A294, R = R A7 , in L A295, R = R A8 ,

in L A335, R = R A7 , in L A336, R = R A8 ,

in L A255, R = R A9 , in L A256 , R = R A10 ,

in L A296, R = R A9 , in L A297, R = R A10 ,

in L A337, R = R A9 , in L A338, R = R A10 ,

in L A257, R = R A11 , in L A258 , R = R A12 ,

in L A298, R = R A11 , in L A299, R = R A12 ,

in L A339, R = R A11 , in L A340, R = R A12 ,

in L A259, R = R A13 , in L A260 , R = R A14 ,

in L A300, R = R A13 , in L A301, R = R A14 ,

in L A341, R = R A13 , in L A342, R = R A14 ,

in L A261, R = R A15 , in L A262 , R = R A16 ,

in L A302, R = R A15 , in L A303, R = R A16 ,

in L A343, R = R A15 , in L A344, R = R A16 ,

in L A263, R = R A17 , in L A264 , R = R A18 ,

in L A304, R = R A17 , in L A305, R = R A18 ,

in L A345, R = R A17 , in L A346, R = R A18 ,

in L A265, R = R A19 , in L A266 , R = R A20 ,

in L A306, R = R A19 , in L A307, R = R A20 ,

in L A347, R = R A19 , in L A348, R = R A20 ,

in L A267, R = R A21 , in L A268 , R = R A22 ,

in L A308, R = R A21 , in L A309, R = R A22 ,

in L A349, R = R A21 , in L A350, R = R A22 ,

in L A269, R = R A23 , in L A270 , R = R A24 ,

in L A310, R = R A23 , in L A311, R = R A24 ,

in L A351, R = R A23 , in L A352, R = R A24 ,

in L A271, R = R A25 , in L A272 , R = R A26 ,

in L A312, R = R A25 , in L A313, R = R A26 ,

in L A353, R = R A25 , in L A354, R = R A26 ,

in L A273, R = R A27 , in L A274 , R = R A28 ,

in L A314, R = R A27 , in L A315, R = R A28 ,

in L A355, R = R A27 , in L A356, R = R A28 ,

in L A275, R = R A29 , in L A276 , R = R A30 ,

in L A316, R = R A29 , in L A317, R = R A30 ,

in L A357, R = R A29 , in L A358, R = R A30 ,

in L A277, R = R A31 , in L A278 , R = R A32 ,

in L A318, R = R A31 , in L A319, R = R A32 ,

in L A359, R = R A31 , in L A360, R = R A32 ,

in L A279, R = R A33 , in L A280 , R = R A34 ,

in L A320, R = R A33 , in L A321, R = R A34 ,

in L A361, R = R A33 , in L A362, R = R A34 ,

in L A281, R = R A35 , in L A282 , R = R A36 ,

in L A322, R = R A35 , in L A323, R = R A36 ,

in L A363, R = R A35 , in L A364, R = R A35 ,

in L A283, R = R A37 , in L A284 , R = R A38 ,

in L A324, R = R A37 , in L A325, R = R A38 ,

in L A365, R = R A37 , in L A366, R = R A38 ,

in L A285, R = R A39 , in L A286 , R = R A40 ,

in L A326, R = R A39 , in L A327, R = R A40 ;

in L A367, R = R A39 , in L A368, R = R A40 ,

and in L A287 , R = R A41 ;      ,

and in L A328 , R = R A41 ;      ,

and in L A369 , R = R A41 ;      ,

L A370 through L A410 , each

L A411 through L A451 , each

represented by the formula

represented by the formula

wherein

wherein

in L A370, R = R A1 , in L A371 , R = R A2 ,

in L A411, R = R A1 , in L A412, R = R A2 ,

in L A372, R = R A3 , in L A373 , R = R A4 ,

in L A413, R = R A3 , in L A414, R = R A4 ,

in L A374, R = R A5 , in L A375 , R = R A6 ,

in L A415, R = R A5 , in L A416, R = R A6 ,

in L A376, R = R A7 , in L A377 , R = R A8 ,

in L A417, R = R A7 , in L A418, R = R A8 ,

in L A378, R = R A9 , in L A379 , R = R A10 ,

in L A419, R = R A9 , in L A420, R = R A10 ,

in L A380, R = R A11 , in L A381 , R = R A12 ,

in L A421, R = R A11 , in L A422, R = R A12 ,

in L A382, R = R A13 , in L A383 , R = R A14 ,

in L A423, R = R A13 , in L A424, R = R A14 ,

in L A384, R = R A15 , in L A385 , R = R A16 ,

in L A425, R = R A15 , in L A426, R = R A16 ,

in L A386, R = R A17 , in L A387 , R = R A18 ,

in L A427, R = R A17 , in L A428, R = R A18 ,

in L A388, R = R A19 , in L A389 , R = R A20 ,

in L A429, R = R A19 , in L A430, R = R A20 ,

in L A390, R = R A21 , in L A391 , R = R A22 ,

in L A431, R = R A21 , in L A432, R = R A22 ,

in L A392, R = R A23 , in L A393 , R = R A24 ,

in L A433, R = R A23 , in L A434, R = R A24 ,

in L A394, R = R A25 , in L A395 , R = R A26 ,

in L A435, R = R A25 , in L A436, R = R A26 ,

in L A396, R = R A27 , in L A397 , R = R A28 ,

in L A437, R = R A27 , in L A438, R = R A28 ,

in L A398, R = R A29 , in L A399 , R = R A30 ,

in L A439, R = R A29 , in L A440, R = R A30 ,

in L A400, R = R A31 , in L A401 , R = R A32 ,

in L A441, R = R A31 , in L A442, R = R A32 ,

in L A402, R = R A33 , in L A403 , R = R A34 ,

in L A443, R = R A33 , in L A444, R = R A34 ,

in L A404, R = R A35 , in L A405 , R = R A36 ,

in L A445, R = R A35 , in L A446, R = R A36 ,

in L A406, R = R A37 , in L A407 , R = R A38 ,

in L A447, R = R A37 , in L A448, R = R A38 ,

in L A408, R = R A39 , in L A409 , R = R A40 ,

in L A449, R = R A39 , in L A450, R = R A40 ;

and in L A410 , R = R A41 ;       , and

and in L A451 , R = R A41 ;      ,

wherein, R A1 through R A41 have the formulas:

21. The composition of claim 1 , wherein the first compound has the formula of Ir(L 1 ) 2 (L 2 ), wherein L 1 is selected from the group consisting of

L A1 through L A41 , each

L A42 through L A82 , each

L A83 through L A123 , each

represented by the formula

represented by the formula

repesented by the formula

wherein

wherein

wherein

in L A1 , R = R A1 , in L A2 , R = R A2 ,

in L A42 , R = R A1 , in L A43 , R = R A2 ,

in L A83 , R = R A1 , in L A84 , R = R A2 ,

in L A3 , R = R A3 , in L A4 , R = R A4 ,

in L A44 , R = R A3 , in L A45 , R = R A4 ,

in L A85 , R = R A3 , in L A86 , R = R A4 ,

in L A5 , R = R A5 , in L A6 , R = R A6 ,

in L A46 , R = R A5 , in L A47 , R = R A6 ,

in L A87 , R = R A5 , in L A88 , R = R A6 ,

in L A7 , R = R A7 , in L A8 , R = R A8 ,

in L A48 , R = R A7 , in L A49 , R = R A8 ,

in L A89 , R = R A7 , in L A90 , R = R A8 ,

in L A9 , R = R A9 , in L A10 , R = R A10 ,

in L A50 , R = R A9 , in L A51 , R = R A10 ,

in L A91 , R = R A9 , in L A92 , R = R A10 ,

in L A11 , R = R A11 , in L A12 , R = R A12 ,

in L A52 , R = R A11 , in L A53 , R = R A12 ,

in L A93 , R = R A11 , in L A94 , R = R A12 ,

in L A13 , R = R A13 , in L A14 , R = R A14 ,

in L A54 , R = R A13 , in L A55 , R = R A14 ,

in L A95 , R = R A13 , in L A96 , R = R A14 ,

in L A15 , R = R A15 , in L A16 , R = R A16 ,

in L A56 , R = R A15 , in L A57 , R = R A16 ,

in L A97 , R = R A15 , in L A98 , R = R A16 ,

in L A17 , R = R A17 , in L A18 , R = R A18 ,

in L A58 , R = R A17 , in L A59 , R = R A18 ,

in L A99 , R = R A17 , in L A100 , R = R A18 ,

in L A19 , R = R A19 , in L A20 , R = R A20 ,

in L A60 , R = R A19 , in L A61 , R = R A20 ,

in L A101 , R = R A19 , in L A102 , R = R A20 ,

in L A21 , R = R A21 , in L A22 , R = R A22 ,

in L A62 , R = R A21 , in L A63 , R = R A22 ,

in L A103 , R = R A21 , in L A104 , R = R A22 ,

in L A23 , R = R A23 , in L A24 , R = R A24 ,

in L A64 , R = R A23 , in L A65 , R = R A24 ,

in L A105 , R = R A23 , in L A106 , R = R A24 ,

in L A25 , R = R A25 , in L A26 , R = R A26 ,

in L A66 , R = R A25 , in L A67 , R = R A26 ,

in L A107 , R = R A25 , in L A108 , R = R A26 ,

in L A27 , R = R A27 , in L A28 , R = R A28 ,

in L A68 , R = R A27 , in L A69 , R = R A28 ,

in L A109 , R = R A27 , in L A110 , R = R A28 ,

in L A29 , R = R A29 , in L A30 , R = R A30 ,

in L A70 , R = R A29 , in L A71 , R = R A30 ,

in L A111 , R = R A29 , in L A112 , R = R A30 ,

in L A31 , R = R A31 , in L A32 , R = R A32 ,

in L A72 , R = R A31 , in L A73 , R = R A32 ,

in L A113 , R = R A31 , in L A114 , R = R A32 ,

in L A33 , R = R A33 , in L A34 , R = R A34 ,

in L A74 , R = R A33 , in L A75 , R = R A34 ,

in L A115 , R = R A33 , in L A116 , R = R A34 ,

in L A35 , R = R A35 , in L A36 , R = R A36 ,

in L A76 , R = R A35 , in L A77 , R = R A36 ,

in L A117 , R = R A35 , in L A118 , R = R A35 ,

in L A37 , R = R A37 , in L A38 , R = R A38 ,

in L A78 , R = R A37 , in L A79 , R = R A38 ,

in L A119 , R = R A37 , in L A120 , R = R A38 ,

in L A39 , R = R A39 , in L A40 , R = R A40 ,

in L A80 , R = R A39 , in L A81 , R = R A40 ;

in L A121 , R = R A39 , in L A122 , R = R A40 ,

and in L A41 , R = R A41 ;      ,

and in L A82 , R = R A41 ;      ,

and in L A123 , R = R A41 ;      ,

L A124 through L A164 , each

L A165 through L A205 , each

L A206 through L A246 , each

represented by the formula

represented by the formula

repesented by the formula

wherein

wherein

wherein

in L A124, R = R A1 , in L A125 , R = R A2 ,

in L A165, R = R A1 , in L A166, R = R A2 ,

in L A206, R = R A1 , in L A207, R = R A2 ,

in L A126, R = R A3 , in L A127 , R = R A4 ,

in L A167, R = R A3 , in L A168, R = R A4 ,

in L A208, R = R A3 , in L A209, R = R A4 ,

in L A128, R = R A5 , in L A129 , R = R A6 ,

in L A169, R = R A5 , in L A170, R = R A6 ,

in L A210, R = R A5 , in L A211, R = R A6 ,

in L A130, R = R A7 , in L A131 , R = R A8 ,

in L A171, R = R A7 , in L A172, R = R A8 ,

in L A212, R = R A7 , in L A213, R = R A8 ,

in L A132, R = R A9 , in L A133 , R = R A10 ,

in L A173, R = R A9 , in L A174, R = R A10 ,

in L A214, R = R A9 , in L A215, R = R A10 ,

in L A134, R = R A11 , in L A135 , R = R A12 ,

in L A175, R = R A11 , in L A176, R = R A12 ,

in L A216, R = R A11 , in L A217, R = R A12 ,

in L A136, R = R A13 , in L A137 , R = R A14 ,

in L A177, R = R A13 , in L A178, R = R A14 ,

in L A218, R = R A13 , in L A219, R = R A14 ,

in L A138, R = R A15 , in L A139 , R = R A16 ,

in L A179, R = R A15 , in L A180, R = R A16 ,

in L A220, R = R A15 , in L A221, R = R A16 ,

in L A140, R = R A17 , in L A141 , R = R A18 ,

in L A181, R = R A17 , in L A182, R = R A18 ,

in L A222, R = R A17 , in L A223, R = R A18 ,

in L A142, R = R A19 , in L A143 , R = R A20 ,

in L A183, R = R A19 , in L A184, R = R A20 ,

in L A224, R = R A19 , in L A225, R = R A20 ,

in L A144, R = R A21 , in L A145 , R = R A22 ,

in L A185, R = R A21 , in L A186, R = R A22 ,

in L A226, R = R A21 , in L A227, R = R A22 ,

in L A146, R = R A23 , in L A147 , R = R A24 ,

in L A187, R = R A23 , in L A188, R = R A24 ,

in L A228, R = R A23 , in L A229, R = R A24 ,

in L A148, R = R A25 , in L A149 , R = R A26 ,

in L A189, R = R A25 , in L A190, R = R A26 ,

in L A230, R = R A25 , in L A231, R = R A26 ,

in L A150, R = R A27 , in L A151 , R = R A28 ,

in L A191, R = R A27 , in L A192, R = R A28 ,

in L A232, R = R A27 , in L A233, R = R A28 ,

in L A152, R = R A29 , in L A153 , R = R A30 ,

in L A193, R = R A29 , in L A194, R = R A30 ,

in L A234, R = R A29 , in L A235, R = R A30 ,

in L A154, R = R A31 , in L A155 , R = R A32 ,

in L A195, R = R A31 , in L A196, R = R A32 ,

in L A236, R = R A31 , in L A237, R = R A32 ,

in L A156, R = R A33 , in L A157 , R = R A34 ,

in L A197, R = R A33 , in L A198, R = R A34 ,

in L A238, R = R A33 , in L A239, R = R A34 ,

in L A158, R = R A35 , in L A159 , R = R A36 ,

in L A199, R = R A35 , in L A200, R = R A36 ,

in L A240, R = R A35 , in L A241, R = R A35 ,

in L A160, R = R A37 , in L A161 , R = R A38 ,

in L A201, R = R A37 , in L A202, R = R A38 ,

in L A242, R = R A37 , in L A243, R = R A38 ,

in L A162, R = R A39 , in L A163 , R = R A40 ,

in L A203, R = R A39 , in L A204, R = R A40 ;

in L A244, R = R A39 , in L A245, R = R A40 ,

and in L A164 , R = R A41 ;      ,

and in L A205 , R = R A41 ;      ,

and in L A246 , R = R A41 ;      ,

L A247 through L A287 , each

L A288 through L A328 , each

L A329 through L A369 , each

represented by the formula

represented by the formula

repesented by the formula

wherein

wherein

wherein

in L A247, R = R A1 , in L A248 , R = R A2 ,

in L A288, R = R A1 , in L A289, R = R A2 ,

in L A329, R = R A1 , in L A330, R = R A2 ,

in L A249, R = R A3 , in L A250 , R = R A4 ,

in L A290, R = R A3 , in L A291, R = R A4 ,

in L A331, R = R A3 , in L A332, R = R A4 ,

in L A251, R = R A5 , in L A252 , R = R A6 ,

in L A292, R = R A5 , in L A293, R = R A6 ,

in L A333, R = R A5 , in L A334, R = R A6 ,

in L A253, R = R A7 , in L A254 , R = R A8 ,

in L A294, R = R A7 , in L A295, R = R A8 ,

in L A335, R = R A7 , in L A336, R = R A8 ,

in L A255, R = R A9 , in L A256 , R = R A10 ,

in L A296, R = R A9 , in L A297, R = R A10 ,

in L A337, R = R A9 , in L A338, R = R A10 ,

in L A257, R = R A11 , in L A258 , R = R A12 ,

in L A298, R = R A11 , in L A299, R = R A12 ,

in L A339, R = R A11 , in L A340, R = R A12 ,

in L A259, R = R A13 , in L A260 , R = R A14 ,

in L A300, R = R A13 , in L A301, R = R A14 ,

in L A341, R = R A13 , in L A342, R = R A14 ,

in L A261, R = R A15 , in L A262 , R = R A16 ,

in L A302, R = R A15 , in L A303, R = R A16 ,

in L A343, R = R A15 , in L A344, R = R A16 ,

in L A263, R = R A17 , in L A264 , R = R A18 ,

in L A304, R = R A17 , in L A305, R = R A18 ,

in L A345, R = R A17 , in L A346, R = R A18 ,

in L A265, R = R A19 , in L A266 , R = R A20 ,

in L A306, R = R A19 , in L A307, R = R A20 ,

in L A347, R = R A19 , in L A348, R = R A20 ,

in L A267, R = R A21 , in L A268 , R = R A22 ,

in L A308, R = R A21 , in L A309, R = R A22 ,

in L A349, R = R A21 , in L A350, R = R A22 ,

in L A269, R = R A23 , in L A270 , R = R A24 ,

in L A310, R = R A23 , in L A311, R = R A24 ,

in L A351, R = R A23 , in L A352, R = R A24 ,

in L A271, R = R A25 , in L A272 , R = R A26 ,

in L A312, R = R A25 , in L A313, R = R A26 ,

in L A353, R = R A25 , in L A354, R = R A26 ,

in L A273, R = R A27 , in L A274 , R = R A28 ,

in L A314, R = R A27 , in L A315, R = R A28 ,

in L A355, R = R A27 , in L A356, R = R A28 ,

in L A275, R = R A29 , in L A276 , R = R A30 ,

in L A316, R = R A29 , in L A317, R = R A30 ,

in L A357, R = R A29 , in L A358, R = R A30 ,

in L A277, R = R A31 , in L A278 , R = R A32 ,

in L A318, R = R A31 , in L A319, R = R A32 ,

in L A359, R = R A31 , in L A360, R = R A32 ,

in L A279, R = R A33 , in L A280 , R = R A34 ,

in L A320, R = R A33 , in L A321, R = R A34 ,

in L A361, R = R A33 , in L A362, R = R A34 ,

in L A281, R = R A35 , in L A282 , R = R A36 ,

in L A322, R = R A35 , in L A323, R = R A36 ,

in L A363, R = R A35 , in L A364, R = R A35 ,

in L A283, R = R A37 , in L A284 , R = R A38 ,

in L A324, R = R A37 , in L A325, R = R A38 ,

in L A365, R = R A37 , in L A366, R = R A38 ,

in L A285, R = R A39 , in L A286 , R = R A40 ,

in L A326, R = R A39 , in L A327, R = R A40 ;

in L A367, R = R A39 , in L A368, R = R A40 ,

and in L A287 , R = R A41 ;      ,

and in L A328 , R = R A41 ;      ,

and in L A369 , R = R A41 ;      ,

L A370 through L A410 , each

L A411 through L A451 , each

represented by the formula

represented by the formula

wherein

wherein

in L A370, R = R A1 , in L A371 , R = R A2 ,

in L A411, R = R A1 , in L A412, R = R A2 ,

in L A372, R = R A3 , in L A373 , R = R A4 ,

in L A413, R = R A3 , in L A414, R = R A4 ,

in L A374, R = R A5 , in L A375 , R = R A6 ,

in L A415, R = R A5 , in L A416, R = R A6 ,

in L A376, R = R A7 , in L A377 , R = R A8 ,

in L A417, R = R A7 , in L A418, R = R A8 ,

in L A378, R = R A9 , in L A379 , R = R A10 ,

in L A419, R = R A9 , in L A420, R = R A10 ,

in L A380, R = R A11 , in L A381 , R = R A12 ,

in L A421, R = R A11 , in L A422, R = R A12 ,

in L A382, R = R A13 , in L A383 , R = R A14 ,

in L A423, R = R A13 , in L A424, R = R A14 ,

in L A384, R = R A15 , in L A385 , R = R A16 ,

in L A425, R = R A15 , in L A426, R = R A16 ,

in L A386, R = R A17 , in L A387 , R = R A18 ,

in L A427, R = R A17 , in L A428, R = R A18 ,

in L A388, R = R A19 , in L A389 , R = R A20 ,

in L A429, R = R A19 , in L A430, R = R A20 ,

in L A390, R = R A21 , in L A391 , R = R A22 ,

in L A431, R = R A21 , in L A432, R = R A22 ,

in L A392, R = R A23 , in L A393 , R = R A24 ,

in L A433, R = R A23 , in L A434, R = R A24 ,

in L A394, R = R A25 , in L A395 , R = R A26 ,

in L A435, R = R A25 , in L A436, R = R A26 ,

in L A396, R = R A27 , in L A397 , R = R A28 ,

in L A437, R = R A27 , in L A438, R = R A28 ,

in L A398, R = R A29 , in L A399 , R = R A30 ,

in L A439, R = R A29 , in L A440, R = R A30 ,

in L A400, R = R A31 , in L A401 , R = R A32 ,

in L A441, R = R A31 , in L A442, R = R A32 ,

in L A402, R = R A33 , in L A403 , R = R A34 ,

in L A443, R = R A33 , in L A444, R = R A34 ,

in L A404, R = R A35 , in L A405 , R = R A36 ,

in L A445, R = R A35 , in L A446, R = R A36 ,

in L A406, R = R A37 , in L A407 , R = R A38 ,

in L A447, R = R A37 , in L A448, R = R A38 ,

in L A408, R = R A39 , in L A409 , R = R A40 ,

in L A449, R = R A39 , in L A450, R = R A40 ;

and in L A410 , R = R A41 ;       , and

and in L A451 , R = R A41 ;      ,

wherein, R A1 through R A41 have the formulas:

and

wherein L 2 is selected from the group consisting of:

22. The compound of claim 21 , wherein the first compound is selected from the group consisting of Compound 1 through Compound 5,863,

wherein each of Compound x, where x=451j+k−451, k is an integer from 1 to 451, and j is an integer from 1 to 13, has the formula Ir(L Ak ) 2 (L Bj ).

23. The composition of claim 1 , wherein the first compound is selected from the group consisting of

24. A first device comprising a first organic light emitting device, the first organic light emitting device comprising:

an anode;

a cathode; and

an organic layer, disposed between the anode and the cathode, comprising a first compound, wherein the first compound is capable of functioning as a phosphorescent emitter at room temperature;

wherein the first compound has at least one aromatic ring and at least one substituent R;

wherein each of the at least one R is independently selected from the group consisting of partially fluorinated alkyl, partially fluorinated cycloalkyl, and combinations thereof;

wherein each of the at least one R is directly bonded to one of the aromatic rings; and

wherein in each of the at least one R, C having an F attached thereto is separated by at least one carbon atom from the aromatic ring;

wherein the first compound 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;

wherein x is 1, 2, or 3;

wherein y is 0, 1, or 2;

wherein z is 0, 1, or 2;

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

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

wherein R a , R b , R c , and R d independently represent mono, di, tri, or tetra substitution, or no substitution;

wherein R a , R b , R c , and R d are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cvcloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;

wherein two adjacent substituents of R a , R b , R c , and R d are optionally joined to form a ring or form a multidentate ligand; and

wherein at least one of the R a , R b , R c , and R d includes at least one R.

25. The first device of claim 24 , wherein the first compound is selected from the group consisting of

26. The first device of claim 24 , wherein the first device is selected from the group consisting of a consumer product, an electronic component module, an organic light emitting device, and a lighting panel.

27. The first device of claim 24 , wherein the organic layer is an emissive layer and the first compound is an emissive dopant or a non-emissive dopant.

28. The first device of claim 24 , wherein the organic layer further comprises a host; wherein the host comprises a triphenylene containing benzo-fused thiophene or benzo-fused furan;

wherein any substituent in the host material is an unfused substituent independently selected from the group consisting of C n H 2n+1 , OC n H 2n+1 , OAr 1 , N(C n H 2n+1 ) 2 , N(Ar 1 )(Ar 2 ), CH═CH—C n H 2n+1 , C≡C—C n H 2n+1 , Ar 1 , Ar 1 —Ar 2 , C n H 2n —Ar 1 , or no substitution;

wherein n is from 1 to 10; and

wherein Ar 1 and Ar 2 are independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof.

29. The first device of claim 24 , 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, dibenzothiphene, dibenzofuran, dibenzoselenophene, azatriphenylene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.

30. The first device of claim 24 , wherein the organic layer further comprises a host; wherein the host material is selected from the group consisting of:

and combinations thereof.

31. The first device of claim 24 , wherein the organic layer further comprises a host; wherein the host material comprises a metal complex.

32. A formulation comprising the composition of claim 1 .

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 8, 2014
From: BOUDREAULT, PIERRE-LUC T.; YEAGER, WALTER; XIA, CHUANJUN
To: UNIVERSAL DISPLAY CORPORATION
Reel/Frame 033910/0422 →
Continuity (1)
Related Publication 20160104848A1 · Apr 14, 2016